| Identification | More | [Name]
N-(tert-Butoxycarbonyl)-(S)-(+)-3-pyrrolidinol | [CAS]
101469-92-5 | [Synonyms]
1-PYRROLIDINECARBOXYLIC ACID, 3-HYDROXY-, 1,1-DIMETHYLETHYL ESTER, (3S)-
(3S)-(+)-N-BOC-3-HYDROXYPYRROLIDINE
BOC-(S)-3-HYDROXYPYRROLIDINE
N-BOC-(S)-3-HYDROXYPYRROLIDINE
N-T-BOC-(S)-3-HYDROXYPYRROLIDINE
N-(TERT-BUTOXYCARBONYL)-(S)-(+)-3-PYRROLIDINOL
(S)-(+)-1-BOC-3-HYDROXYPYRROLIDINE
(S)-1-BOC-3-HYDROXYPYRROLIDINE
(S)-1-BOC-3-PYRROLIDINOL
(S)-1-N-BOC-3-HYDROXYPYRROLIDINE
(S)-1-N-(T-BUTOXYCARBONYL)-3-HYDROXYPYRROLIDINE
(S)-1-N-(TERT-BUTOXYCARBONYL)-3-HYDROXYPYRROLIDINE
(S)-3-HYDROXY-PYRROLIDINE-1-CARBOXYLIC ACID TERT-BUTYL ESTER
(S)-(+)-BOC-3-PYRROLIDINOL
(S)-N-BOC-3-HYDROXYPYRROLIDINE HYDROCHLORIDE
(S)-N-BOC-3-PYRROLIDINOL
(S)-(+)-N-(TERT-BUTOXYCARBONYL)-3-HYDROXYPYRROLIDINE
(S)-N-(TERT-BUTOXYCARBONYL)-3-HYDROXYPYRROLIDINE
(S)-TERT-BUTYL 3-HYDROXYPYRROLIDINE-1-CARBOXYLATE
(3S)-1-Boc-3-pyrrolidinol~(3S)-1-tert-Butoxycarbonyl-3-hydroxypyrrolidine | [EINECS(EC#)]
600-216-0 | [Molecular Formula]
C9H17NO3 | [MDL Number]
MFCD01317839 | [Molecular Weight]
187.24 | [MOL File]
101469-92-5.mol |
| Chemical Properties | Back Directory | [Appearance]
white to light yellow crystal powde | [Melting point ]
60-64 °C (lit.) | [alpha ]
26 º (c=1%, MeOH) | [Boiling point ]
273.3±33.0 °C(Predicted) | [density ]
1.142±0.06 g/cm3(Predicted) | [refractive index ]
27 ° (C=1, MeOH) | [storage temp. ]
Store at 0-5°C | [solubility ]
soluble in Methanol | [form ]
Crystalline Powder | [pka]
14.74±0.20(Predicted) | [color ]
White to pale yellow | [Optical Rotation]
[α]20/D +26°, c = 1% in methanol | [BRN ]
6271108 | [InChI]
InChI=1S/C9H17NO3/c1-9(2,3)13-8(12)10-5-4-7(11)6-10/h7,11H,4-6H2,1-3H3/t7-/m0/s1 | [InChIKey]
APCBTRDHCDOPNY-ZETCQYMHSA-N | [SMILES]
N1(C(OC(C)(C)C)=O)CC[C@H](O)C1 | [CAS DataBase Reference]
101469-92-5(CAS DataBase Reference) |
| Safety Data | Back Directory | [Symbol(GHS) ]
 
GHS05,GHS06 | [Signal word ]
Danger | [Hazard statements ]
H301-H315-H318-H335 | [Precautionary statements ]
P280-P301+P310+P330-P302+P352-P305+P351+P338+P310 | [Hazard Codes ]
T,Xi | [Risk Statements ]
R25:Toxic if swallowed.
R37/38:Irritating to respiratory system and skin .
R41:Risk of serious damage to eyes. | [Safety Statements ]
S26:In case of contact with eyes, rinse immediately with plenty of water and seek medical advice .
S39:Wear eye/face protection .
S45:In case of accident or if you feel unwell, seek medical advice immediately (show label where possible) . | [RIDADR ]
UN 2811 6.1/PG 3
| [WGK Germany ]
3
| [F ]
10 | [HazardClass ]
6.1 | [PackingGroup ]
Ⅲ | [HS Code ]
29339900 | [Storage Class]
6.1C - Combustible acute toxic Cat.3
toxic compounds or compounds which causing chronic effects | [Hazard Classifications]
Acute Tox. 3 Oral
Eye Dam. 1
Skin Irrit. 2
STOT SE 3 |
| Hazard Information | Back Directory | [Chemical Properties]
white to light yellow crystal powde | [Uses]
(S)-(+)-N-Boc-3-pyrrolidinol can be used as a reactant to synthesize:
- tert-Butyl 3-(2-bromophenoxy)pyrrolidine-1-carboxylate, which is employed as a key intermediate in the preparation of IkB-kinase IKK2 inhibitor.
- Dimethoxy-pyrrolidylquinazoline , and peptidomimetic quinoline derivatives.
| [Synthesis]
The general procedure for the synthesis of 1-tert-butoxycarbonyl-3-hydroxy-pyrrolidine from di-tert-butyl dicarbonate and 3-hydroxy-pyrrolidine was as follows: first, (R)-3-pyrrolidinol (539 mg, 6.19 mmol) was converted into compound 16b to afford a colorless oily substance (1.3 g, 100% yield). The spectral data of this product were consistent with the expected structure and in accordance with literature reports (see Kucznierz, R. et al. J. Med. Chem. 1998, 41, 4983-4994). Subsequently, compound 16b was converted by reaction to compound 16c, again as a colorless oil. Next, compound 16e was prepared from compound 16c by a two-step reaction, still as a colorless oily substance. Finally, compound 16e was further reacted to obtain the target product compound 16, which was rendered as a yellow oily substance. | [References]
[1] ACS Medicinal Chemistry Letters, 2013, vol. 4, # 10, p. 969 - 973
[2] Patent: WO2015/9731, 2015, A2. Location in patent: Paragraph 00106
[3] Journal of Medicinal Chemistry, 1998, vol. 41, # 25, p. 4983 - 4994
[4] Bioorganic and Medicinal Chemistry, 2006, vol. 14, # 17, p. 5812 - 5832
[5] Patent: WO2010/84767, 2010, A1. Location in patent: Page/Page column 86 |
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