[(1S)-1-(t-butyldiphenylsilyloxymethyl)propyl]carbamic acid benzyl ester → (1S)-1-(t-butyldiphenylsilyloxymethyl)propylamine

HRID 891632Notes

Reaction equation

HRID 891632 reaction equation
C(OC(=O)[NH:10][C@H:11]([CH2:14][O:15][Si:16]([C:29]([CH3:32])([CH3:31])[CH3:30])([C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1)[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)[CH2:12][CH3:13])C1C=CC=CC=1>CO.[Pd]>[Si:16]([O:15][CH2:14][C@@H:11]([NH2:10])[CH2:12][CH3:13])([C:29]([CH3:31])([CH3:32])[CH3:30])([C:23]1[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=1)[C:17]1[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=1

Participants

4

Reactant 1

HCID 60109785[(1S)-1-(t-butyldiphenylsilyloxymethyl)propyl]carbamic acid benzyl ester

Product 1

HCID 23598348(1S)-1-(t-butyldiphenylsilyloxymethyl)propylamineYield 88.5%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A solution of [(1S)-1-(t-butyldiphenylsilyloxymethyl)propyl]carbamic acid benzyl ester (3.70 g, 8.00 mmol) (obtained as described in Reference Example 34(1)) in methanol (185 ml) was subjected to catalytic hydrogenation in the presence of 10% palladium on charcoal (3.70 g) at room temperature for 4 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:methanol (9:1) as the eluant to afford (1S)-1-(t-butyldiphenylsilyloxymethyl)propylamine (2.32 g, yield 88%) as a colorless oil.

Workup

  1. customthe completion of the reaction
  2. filtrationthe reaction mixture was filtered in order
  3. customto remove the catalyst
  4. concentrationthe filtrate concentrated under reduced pressure
  5. customThe residue was purified by chromatography on a silica gel column

Sources & evidence

ORD record
ord-fca0f4af0c1846d7bf069eb9c05244f6
Source dataset
uspto-grants-2006_02
Patent number
US07001897B2

Reaction notes

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