Methanol → HCID 68913831, compound

HRID 732625Notes

Reaction equation

C([N:8]1[CH2:12][C@H:11]([C:13]2[CH:18]=[CH:17][CH:16]=[C:15]([C:19]([F:22])([F:21])[F:20])[CH:14]=2)[C@@H:10]([CH2:23][O:24][Si:25]([C:28]([CH3:31])([CH3:30])[CH3:29])([CH3:27])[CH3:26])[CH2:9]1)C1C=CC=CC=1.C([O-])=O.[NH4+].CO>O.[Pd]>[Si:25]([O:24][CH2:23][C@@H:10]1[C@@H:11]([C:13]2[CH:18]=[CH:17][CH:16]=[C:15]([C:19]([F:21])([F:20])[F:22])[CH:14]=2)[CH2:12][NH:8][CH2:9]1)([C:28]([CH3:31])([CH3:30])[CH3:29])([CH3:27])[CH3:26]

Participants

Conditions

Temperature: 50 °C

Procedure

At room temperature, 1.0 g of 10% palladium/carbon was added, while suspending in 10 ml of water, to a mixture of 9.69 g of (3R,4S)-1-benzyl-3-({[tert-butyl(dimethyl)silyl]oxy}methyl)-4-[3-(trifluoromethyl)phenyl]pyrrolidine, 5.70 mg of ammonium formate and 100 ml of methanol. This was vigorously stirred at 50° C. for 4 hours and then cooled down to room temperature, and the insoluble matter was removed by filtration through a celite layer. The filtrate was concentrated under a reduced pressure, and the thus obtained residue was purified by a silica gel column chromatography (chloroform-ethyl acetate) to obtain 7.89 g of (3R,4S)-3-({[tert-butyl(dimethyl)silyl]oxy}methyl)-4-[3-(trifluoromethyl)phenyl]pyrrolidine as a pale yellow oily substance.

Workup

temperaturecooled down to room temperature
customthe insoluble matter was removed by filtration through a celite layer
concentrationThe filtrate was concentrated under a reduced pressure
customthe thus obtained residue was purified by a silica gel column chromatography (chloroform-ethyl acetate)

Sources & evidence

ORD record: ord-556242c3469647edae3f0910f13a4fd8
Source dataset: uspto-grants-2009_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07585886B2

Reaction notes

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