[(1S)-2-(t-butyldiphenylsilyloxy)-1-methylethyl]carbamic acid benzyl ester → (S)-1-((tert-butyldiphenylsilyl)oxy)propan-2-amine
Reaction equation
C(OC(=O)[NH:10][C@@H:11]([CH3:31])[CH2:12][O:13][Si:14]([C:27]([CH3:30])([CH3:29])[CH3:28])([C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)C1C=CC=CC=1>CO.[Pd]>[Si:14]([O:13][CH2:12][C@@H:11]([NH2:10])[CH3:31])([C:27]([CH3:29])([CH3:30])[CH3:28])([C:21]1[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=1)[C:15]1[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=1Participants
4
Procedure
A solution of [(1S)-2-(t-butyldiphenylsilyloxy)-1-methylethyl]carbamic acid benzyl ester (6.71 g, 15.0 mmol) (obtained as described in Reference Example 35(1)) in methanol (340 ml) was subjected to catalytic hydrogenation in the presence of 10% palladium on charcoal (6.71 g) at room temperature for 2.5 hours. After checking the completion of the reaction, the reaction mixture was filtered in order to remove the catalyst and the filtrate concentrated under reduced pressure. The residue was purified by chromatography on a silica gel column using methylene chloride→methylene chloride:methanol (85:15) as the eluant to afford (1S)-2-(t-butyldiphenylsilyloxy)-1-methyl-ethylamine (3.93 g, yield 84%) as a pale yellow oil.
Workup
- customthe completion of the reaction
- filtrationthe reaction mixture was filtered in order
- customto remove the catalyst
- concentrationthe filtrate concentrated under reduced pressure
- customThe residue was purified by chromatography on a silica gel column
Sources & evidence
- ORD record
- ord-0ec714b919b34930848969e6a52eae82
- Source dataset
- uspto-grants-2006_02
- Patent number
- US07001897B2
Reaction notes
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