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(3S,4S)-N-Boc-3-amino-4-hydroxypyrrolidine

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(3S,4S)-N-Boc-3-amino-4-hydroxypyrrolidine Basic information
Product Name:(3S,4S)-N-Boc-3-amino-4-hydroxypyrrolidine
Synonyms:(3s,4s)-n-boc-3-amino-4-hydroxypyrrolidine;1-Pyrrolidinecarboxylicacid,3-amino-4-hydroxy-,1,1-dimethylethylester,(3S,4S)-(9CI);(3S,4S)-3-Amino-4-hydroxypyrrolidine-1-carboxylic acid tert-butyl ester;1-Boc-(3S,4S)-3-aMino-4-hydroxypyrrolidine;(3S,4S)-4-aMino-1-N-tert-butyloxycarbonyl-3-hydroxypyrrolidine;(3S,4S)-N-Boc-4-hydroxypyrrolidine;Trans-(3S,4S)-1-Boc-3-aMino-4-hydroxypyrrolidine;tert-Butyl (3R,4R)-3-amino-4-hydroxypyrrolidine-1-carboxylate 97%
CAS:190792-74-6
MF:C9H18N2O3
MW:202.25
EINECS:
Product Categories:AMINOACID
Mol File:190792-74-6.mol
(3S,4S)-N-Boc-3-amino-4-hydroxypyrrolidine Structure
(3S,4S)-N-Boc-3-amino-4-hydroxypyrrolidine Chemical Properties
Boiling point 308.8±42.0 °C(Predicted)
density 1.179
storage temp. 2-8°C(protect from light)
pka14.36±0.40(Predicted)
AppearanceWhite to off-white Solid
Optical Rotation2.4° (C=0.01 g/ml, ETOH)
InChIInChI=1S/C9H18N2O3/c1-9(2,3)14-8(13)11-4-6(10)7(12)5-11/h6-7,12H,4-5,10H2,1-3H3/t6-,7-/m0/s1
InChIKeyMOZOQDNRVPHFOO-BQBZGAKWSA-N
SMILESN1(C(OC(C)(C)C)=O)C[C@H](O)[C@@H](N)C1
Safety Information
MSDS Information
(3S,4S)-N-Boc-3-amino-4-hydroxypyrrolidine Usage And Synthesis
Uses(3S,4S)-N-Boc-3-amino-4-hydroxypyrrolidine is used as a pharmaceutical intermediate.
Synthesis
1-Pyrrolidinecarboxylic acid, 3-azido-4-[(trimethylsilyl)oxy]-, 1,1-dimethylethyl ester, (3S,4S)-

1202067-33-1

(3S,4S)-N-Boc-3-amino-4-hydroxypyrrolidine

190792-74-6

General procedure for the synthesis of 1-Boc-(3S,4S)-3-amino-4-hydroxypyrrolidine from the compound (CAS:1202067-33-1): trifluoroacetic acid (TFA, 3 drops) was added to a methanol (50 mL) solution of Intermediate 11 (5.1 g, 17.1 mmol) and the mixture was stirred for 2 hours. Subsequently, platinum oxide (100 mg, 0.44 mmol) was added to the mixture and stirred under hydrogen atmosphere for 18 hours. After completion of the reaction, the mixture was filtered through diatomaceous earth and the solvent was removed by vacuum evaporation. The crude product was recrystallized by dichloromethane (DCM) to afford 1-Boc-(3S,4S)-3-amino-4-hydroxypyrrolidine as a white solid (2.42 g, 71% yield). NMR hydrogen spectral (CDCl3) data: δ 3.99 (1H, m), 3.70 (2H, m), 3.34 (2H, m), 3.12 (1H, m), 1.48 (9H, s).

References[1] Patent: WO2009/153554, 2009, A1. Location in patent: Page/Page column 40
(3S,4S)-N-Boc-3-amino-4-hydroxypyrrolidine Preparation Products And Raw materials
Raw materials1-Pyrrolidinecarboxylic acid, 3-azido-4-[(trimethylsilyl)oxy]-, 1,1-dimethylethyl ester, (3S,4S)--->Hydrogen-->Trifluoroacetic acid
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