Water → (2S,5R)-2-(4-chlorophenyl)-5-hydroxymethyl-pyrrolidine-1-carboxylic acid t-butyl ester

HRID 1677073Notes

Reaction equation

HRID 1677073 reaction equation
O1CCCC1.C([O:8][C:9](=O)[C@H:10]([NH:22][C:23]([O:25][C:26]([CH3:29])([CH3:28])[CH3:27])=[O:24])[CH2:11][CH2:12][C:13]([C:15]1[CH:20]=[CH:19][C:18]([Cl:21])=[CH:17][CH:16]=1)=O)C.O>C(OCC)(=O)C>[C:26]([O:25][C:23]([N:22]1[C@@H:10]([CH2:9][OH:8])[CH2:11][CH2:12][C@H:13]1[C:15]1[CH:20]=[CH:19][C:18]([Cl:21])=[CH:17][CH:16]=1)=[O:24])([CH3:29])([CH3:28])[CH3:27]

Participants

5

Reactant 3

HCID 962WaterHCID 8028TetrahydrofuranHCID 67371186ethyl (R)-2-tert-butoxycarbonylamino-5-(4-chlorophenyl)-5-oxopentanoate

Product 1

HCID 67375406(2S,5R)-2-(4-chlorophenyl)-5-hydroxymethyl-pyrrolidine-1-carboxylic acid t-butyl esterYield 104.4%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

Ice-cold lithium borohydride (277 mg) was added to a tetrahydrofuran (40 mL) solution of (2R,5S)-5-(4-chlorophenyl)pyrrolidine-1,2-dicarboxylic acid 1-t-butyl ester 2-ethyl ester (3 g) obtained in Example 8. Stirring was continued for 30 minutes at the same temperature and for 13 hours at room temperature. Water and ethyl acetate were added, and the organic layer was partitioned. The organic layer was washed with brine and was dried over anhydrous magnesium sulfate. The solvent was removed under a vacuum, and the title compound (2.64 g) was obtained. The physical property values are as follows.

Workup

  1. customthe organic layer was partitioned
  2. washThe organic layer was washed with brine
  3. dry with materialwas dried over anhydrous magnesium sulfate
  4. customThe solvent was removed under a vacuum

Sources & evidence

ORD record
ord-091702770f6f4cf980bbafe4dc6f797a
Source dataset
uspto-grants-2011_08
Patent number
US08008293B2

Reaction notes

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