tert-Butyl 4-(3-hydroxypropyl)tetrahydro-1(2H)-pyridinecarboxylate

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tert-Butyl 4-(3-hydroxypropyl)tetrahydro-1(2H)-pyridinecarboxylate Basic information
Product Name:tert-Butyl 4-(3-hydroxypropyl)tetrahydro-1(2H)-pyridinecarboxylate
Synonyms:4-(3-HYDROXY-PROPYL)-PIPERIDINE-1-CARBOXYLIC ACID TERT-BUTYL ESTER;1-N-BOC-4-(3'-PROPANOL)-PIPERIDINE;4-(3-Hydroxypropyl)piperidine, N-BOC protected;Tert-butyl 4-(3-hydroxypropyl)tetrahydro-1(2H)-pyridinecarboxylate ,97%;3-(1-(tert-Butoxycarbonyl)piperidin-4-yl)propanol;3-(N-Boc-piperidin-4-yl)propanol;tert-Butyl 4-(3-hydroxypropyl)tetrahydropyridine-1(2H)-carboxylate;1-Piperidinecarboxylic acid, 4-(3-hydroxypropyl)-, 1,1-diMethylethyl ester
CAS:156185-63-6
MF:C13H25NO3
MW:243.34
EINECS:
Product Categories:Pyrans, Piperidines &Piperazines;Pyrans, Piperidines & Piperazines;CMLLYL
Mol File:156185-63-6.mol
tert-Butyl 4-(3-hydroxypropyl)tetrahydro-1(2H)-pyridinecarboxylate Structure
tert-Butyl 4-(3-hydroxypropyl)tetrahydro-1(2H)-pyridinecarboxylate Chemical Properties
Boiling point 339.8±15.0 °C(Predicted)
density 1.029
storage temp. 2-8°C
solubility Chloroform (Slightly), Methanol (Slightly)
pka15.16±0.10(Predicted)
form Low-Melting Solid
color White to Off-White
InChIInChI=1S/C13H25NO3/c1-13(2,3)17-12(16)14-8-6-11(7-9-14)5-4-10-15/h11,15H,4-10H2,1-3H3
InChIKeyOXPWHPCCUXESFQ-UHFFFAOYSA-N
SMILESN1(C(OC(C)(C)C)=O)CCC(CCCO)CC1
Safety Information
Hazard Codes Xi
Risk Statements 36/37/38
Safety Statements 26-36/37/39
Hazard Note Irritant
HS Code 2933399990
MSDS Information
tert-Butyl 4-(3-hydroxypropyl)tetrahydro-1(2H)-pyridinecarboxylate Usage And Synthesis
Usestert-Butyl 4-(3-Hydroxypropyl)piperidine-1-carboxylate is a reagent in the preparation of 1-alkyloxy-2-methoxy-4-nitrobenzene fragments: potent human glutaminyl cyclase inhibitors.
Synthesis
piperidine-4-propanol

7037-49-2

Di-tert-butyl dicarbonate

24424-99-5

TERT-BUTYL 4-(3-HYDROXYPROPYL)TETRAHYDRO-1(2H)-PYRIDINECARBOXYLATE

156185-63-6

The general procedure for the synthesis of N-BOC-4-(3'-hydroxypropyl)-piperidine from 3-(4-piperidinyl)-1-propanol and di-tert-butyl dicarbonate was as follows: 1. Di-tert-butyl dicarbonate (3.66 g, 16.8 mmol) was slowly added to a stirring solution of anhydrous dichloromethane (20 mL) of 3-(4-piperidinyl)-1-propanol (1.60 g, 11.2 mmol) under nitrogen protection and the reaction was carried out at ambient temperature. 2. The resulting reaction mixture was stirred continuously for 2 hours. 3. Upon completion of the reaction, the mixture was purified directly by silica gel column chromatography with the eluent being methanol in dichloromethane (0-3% gradient). 4. The target fraction was collected to afford N-BOC-4-(3'-hydroxypropyl)-piperidine as a clear oil (2.40 g, 88% yield).

References[1] Organic Letters, 2002, vol. 4, # 4, p. 549 - 552
[2] Patent: US2008/306082, 2008, A1. Location in patent: Page/Page column 5-6
[3] Patent: US6235731, 2001, B1
[4] Organic and Biomolecular Chemistry, 2014, vol. 12, # 5, p. 783 - 794
[5] Tetrahedron, 1999, vol. 55, # 39, p. 11619 - 11639
tert-Butyl 4-(3-hydroxypropyl)tetrahydro-1(2H)-pyridinecarboxylate Preparation Products And Raw materials
Raw materialspiperidine-4-propanol-->Methyl N-Boc-4-piperidinepropionate-->Di-tert-butyl dicarbonate
Preparation Products1-Boc-4-(3-broMopropyl)piperidine-->piperidine-4-propanol
Tag:tert-Butyl 4-(3-hydroxypropyl)tetrahydro-1(2H)-pyridinecarboxylate(156185-63-6) Related Product Information
4-(2-Ethoxycarbonyl-acetyl)-piperidine-1-carboxylic acid tert-butyl ester Methyl N-Boc-4-piperidinepropionate tert-Butyl 4-(3-hydroxypropyl)tetrahydro-1(2H)-pyridinecarboxylate tert-Butyl formate piperidine-4-propanol N-Boc-4-piperidinepropionic acid 4'-N-Boc-spiro-indane-piperidine-3-carboxylic acid Ethyl 3-(1-Boc-piperidine-4-yl)-DL-beta-alaninate N-Boc-1-oxa-8-aza-spiro[4.5]decan-3-ol N-alpha-Fmoc-beta-(1-Boc-piperidin-4-yl)-D,L-alanine 4-(2-Ethoxycarbonyl-1-acetyl)-piperidine-1-carboxylic acid tertio-butyl ester 2-(1-(tert-Butoxycarbonyl)piperidin-4-yl)cyclohexanecarboxylic acid L-Ala-4PIP(Boc)-OMe 4-[2-Carboxy-1-(9H-fluoren-9-ylmethoxycarbonylamino)-ethyl]-piperidine-1-carboxylic acid tert-butyl ester (S)-N-alpha-N'-Di-t-butyloxycarbonyl-4-piperidylalanine 4-(1-Benzyloxycarbonylamino-2-carboxy-ethyl)-piperidine-1-carboxylic acid tert-butyl ester 4-(1-Amino-2-carboxy-ethyl)-piperidine-1-carboxylic acid tert-butyl ester Boc-(3S, 3R)-3-amino-[3-(4-pip(Boc))]propionic acid