Water → HCID 59838273, compound

HRID 1372588Notes

Reaction equation

CSC.B.[C:5]([O:9][C:10]([N:12]1[CH2:16][C@@H:15]([O:17][C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[CH2:14][C@H:13]1[C:24](O)=[O:25])=[O:11])([CH3:8])([CH3:7])[CH3:6].O>C1COCC1>[C:5]([O:9][C:10]([N:12]1[CH2:16][C@@H:15]([O:17][C:18]2[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=2)[CH2:14][C@H:13]1[CH2:24][OH:25])=[O:11])([CH3:8])([CH3:7])[CH3:6]

Participants

Conditions

Temperature: 0 °C

Procedure

Borane-dimethyl sulfide (1.55 ml, 15.5 mmol) was added to a solution of (2S,4S)-1-tert-butoxycarbonyl-4-phenoxy-2-pyrrolidinylcarboxylic acid (2.39 g, 7.76 mmol) in THF (50 ml) under stirring at 0° C. The reaction mixture was stirred at the same temperature for 10 minutes and then at 50° C. for 2 hours. After cooling the reaction mixture to 0° C., water (30 ml) was added thereto, followed by extraction with ethyl acetate. The extract was washed with saturated brine, dried over anhydrous sodium sulfate and distilled under reduced pressure to remove the solvent. The residue was purified by chromatography on a silica gel column (silica gel: 60 g), whereby from chloroform/methanol (50/1) eluate fractions, the title compound (2.83 g, 100%) was obtained as a colorless oil.

Workup

stirringThe reaction mixture was stirred at the same temperature for 10 minutes
temperatureAfter cooling the reaction mixture to 0° C.
extractionfollowed by extraction with ethyl acetate
washThe extract was washed with saturated brine
dry with materialdried over anhydrous sodium sulfate
distillationdistilled under reduced pressure
customto remove the solvent
customThe residue was purified by chromatography on a silica gel column (silica gel: 60 g), whereby from chloroform/methanol (50/1) eluate fractions

Sources & evidence

ORD record: ord-35941b422e504e5b97766c5ebbb1f045
Source dataset: uspto-grants-2007_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07157487B2

Reaction notes

Loading…