HCID 69583498, compound → HCID 23598350, compound

HRID 891661Notes

Reaction equation

HRID 891661 reaction equation
C(OC(=O)[NH:10][C@H:11]([CH2:16][O:17][Si:18]([C:31]([CH3:34])([CH3:33])[CH3:32])([C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1)[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)[C@@H:12]([CH3:15])[CH2:13][CH3:14])C1C=CC=CC=1>CO.[Pd]>[Si:18]([O:17][CH2:16][C@@H:11]([NH2:10])[C@@H:12]([CH3:15])[CH2:13][CH3:14])([C:31]([CH3:33])([CH3:34])[CH3:32])([C:25]1[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=1)[C:19]1[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=1

Participants

4

Reactant 1

HCID 69583498HCID 69583498, compound

Product 1

HCID 23598350HCID 23598350, compoundYield 83%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A solution of [(1S,2S)-1-(t-butyldiphenylsilyloxymethyl)-2-methylbutyl]carbamic acid benzyl ester (6.72 g, 13.7 mmol) (obtained as described in Reference Example 38(1)) in methanol (200 ml) was subjected to catalytic hydrogenation in the presence of 10% palladium on charcoal (6.72 g) at room temperature for 2 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 (98:2→9:1) as the eluant to afford (1S,2S)-1-(t-butyldiphenylsilyloxymethyl)-2-methylbutylamine (4.04 g, yield 83%).

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-5bd1007c7f3e4a4db4e3a50fb9502716
Source dataset
uspto-grants-2006_02
Patent number
US07001897B2

Reaction notes

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