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(R)-N-Boc-piperazine-2-carboxylic acid methyl ester

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(R)-N-Boc-piperazine-2-carboxylic acid methyl ester Basic information
Product Name:(R)-N-Boc-piperazine-2-carboxylic acid methyl ester
Synonyms:(R)-Piperazine-1,2-dicarboxylic acid 1-tert-butyl ester 2-methyl ester (R)-1-Boc-piperazine-2-carboxylic acid methyl ester;[(2-N-BOC)PIPERAZINE(2R)COOH]-OME;(R)-PIPERAZINE-1,2-DICARBOXYLIC ACID 1-TERT-BUTYL ESTER 2-METHYL ESTER;(R)-1-N-BOC-PIPERAZINE-2-CARBOXYLIC ACID METHYL ESTER;(R)-1-TERT-BUTYL 2-METHYL PIPERAZINE-1,2-DICARBOXYLATE;(R)-N-Boc-piperazine-2-carboxylic acid methyl ester;(R)-1--Boc-Piperazine-2-carboxylic acid methyl ester;Methyl (R)-1-Boc-piperazine-2-carboxylate
CAS:252990-05-9
MF:C11H20N2O4
MW:244.29
EINECS:
Product Categories:amino acids;pharmacetical;Piperaizine
Mol File:252990-05-9.mol
(R)-N-Boc-piperazine-2-carboxylic acid methyl ester Structure
(R)-N-Boc-piperazine-2-carboxylic acid methyl ester Chemical Properties
Boiling point 321.3±37.0 °C(Predicted)
density 1.118±0.06 g/cm3(Predicted)
storage temp. 2-8°C(protect from light)
pka7.25±0.40(Predicted)
AppearanceColorless to light yellow Liquid
InChIInChI=1S/C11H20N2O4/c1-11(2,3)17-10(15)13-6-5-12-7-8(13)9(14)16-4/h8,12H,5-7H2,1-4H3/t8-/m1/s1
InChIKeyBRXKHIPPSTYCKO-MRVPVSSYSA-N
SMILESN1(C(OC(C)(C)C)=O)CCNC[C@@H]1C(OC)=O
CAS DataBase Reference252990-05-9(CAS DataBase Reference)
Safety Information
HS Code 2933599590
MSDS Information
(R)-N-Boc-piperazine-2-carboxylic acid methyl ester Usage And Synthesis
Synthesis
(R)-4-Boc-Piperazine-3-carboxylic acid

278788-60-6

(TRIMETHYLSILYL)DIAZOMETHANE

18107-18-1

(R)-N-Boc-piperazine-2-carboxylic acid methyl ester

252990-05-9

Trimethylsilylated diazomethane (2 M solution in hexane, 14 mL) was slowly added dropwise to a mixture of (R)-N-Boc-2-piperazinecarboxylic acid (5 g) dissolved in methanol (100 mL) and dichloromethane (115 mL). The reaction mixture was stirred at room temperature for 16 hours. Upon completion of the reaction, the solvent was removed by distillation under reduced pressure and the residue obtained was purified by column chromatography, first using ethyl acetate as eluent and subsequently using a solution of ethyl acetate containing 5% methanol and 7N ammonia as eluent to afford methyl (R)-1-Boc-2-piperazinecarboxylate as an oil (2.55 g, 48% yield). NMR hydrogen spectrum (DMSO-d6) δ 1.40 (s, 9H), 2.10 (bs, 1H), 2.52 (m, 1H), 2.72 (dd, 1H), 2.82 (d, 1H), 2.97 (m, 1H), 3.29 (d, 1H), 3.61 (d, 1H), 3.67 (s, 3H), 4.43 (m, 1H); mass spectrum showed the molecular ion peak MH+ 245.

References[1] Patent: WO2005/26152, 2005, A1. Location in patent: Page/Page column 136
(R)-N-Boc-piperazine-2-carboxylic acid methyl ester Preparation Products And Raw materials
Raw materials(R)-4-Boc-Piperazine-3-carboxylic acid-->(Trimethylsilyl)diazomethane
Preparation Products(R)-1-N-Boc-2-(hydroxymethyl)piperazine
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