Water → 1-Tert-butyloxycarbonyl-cis-2-formyl-5-phenylpyrrolidine

HRID 1162829Notes

Reaction equation

[C:1]([O:5][C:6]([N:8]1[C@H:12]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[CH2:11][CH2:10][C@@H:9]1[C:19](N(OC)C)=[O:20])=[O:7])([CH3:4])([CH3:3])[CH3:2].[H-].[H-].[H-].[H-].[Li+].[Al+3].S(=O)(=O)(O)[O-].[K+].O>C1COCC1.CCOC(C)=O>[C:1]([O:5][C:6]([N:8]1[C@H:12]([C:13]2[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=2)[CH2:11][CH2:10][C@@H:9]1[CH:19]=[O:20])=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

Conditions

Temperature: 0 °C

Procedure

To a cold (−78° C.) solution of 1-tert-butyloxycarbonyl-cis-2-{[methoxy(methyl)amino]carbonyl}-5-phenylpyrrolidine (1.36 g, 4.07 mmol) in THF (20 mL) under an atmosphere of nitrogen, a 1M solution of LAH in THF (4.07 mL, 4.07 mmol) was added dropwise and the mixture was stirred for 30 min. The mixture was warmed to 0° C. for 30 min and then quenched with potassium bisulfate solution in water (0.969 g, 7.12 mmol). EtOAc was added and the organic phase was separated, washed with brine, dried over anhydrous sodium sulfate, filtered, and concentrated under vacuum. The residue was subjected to column chromatography on silica gel eluting with a 50:50 mixture of ethyl acetate and hexane. Collection and concentration of appropriate fractions provided 1-tert-butyloxycarbonyl-cis-2-formyl-5-phenylpyrrolidine. HPLC RT=3.47 min, 99% at 215 nm (Method A); ES MS (M+H)=276.3.

Workup

customthe organic phase was separated
washwashed with brine
dry with materialdried over anhydrous sodium sulfate
filtrationfiltered
concentrationconcentrated under vacuum
additionThe residue was subjected to column chromatography on silica gel eluting with a 50:50 mixture of ethyl acetate and hexane
customCollection and concentration of appropriate fractions

Sources & evidence

ORD record: ord-ee4ff0ff38904d3f83c0e766d51ee13b
Source dataset: uspto-grants-2010_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07820680B2

Reaction notes

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