N-[2-(t-butyldiphenylsilyloxy)ethyl]-N-methyl-carbamic acid benzyl ester → 2-(tert-butyldiphenylsilyloxy)-N-methylethanamine

HRID 891676Notes

Reaction equation

HRID 891676 reaction equation
C(O[C:9](=O)[N:10]([CH2:12][CH2:13][O:14][Si:15]([C:28]([CH3:31])([CH3:30])[CH3:29])([C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)C)C1C=CC=CC=1>CO.[Pd]>[Si:15]([O:14][CH2:13][CH2:12][NH:10][CH3:9])([C:28]([CH3:30])([CH3:31])[CH3:29])([C:22]1[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=1)[C:16]1[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=1

Participants

4

Reactant 1

HCID 69544211N-[2-(t-butyldiphenylsilyloxy)ethyl]-N-methyl-carbamic acid benzyl ester

Product 1

HCID 118231582-(tert-butyldiphenylsilyloxy)-N-methylethanamineYield 69%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A solution of N-[2-(t-butyldiphenylsilyloxy)-ethyl]-N-methyl-carbamic acid benzyl ester (5.7 g, 12.7 mmol) (obtained as described in Reference Example 40(1)) in methanol (285 ml) was subjected to catalytic hydrogenation in the presence of 10% palladium on charcoal (5.7 g) at room temperature. 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 ethyl acetate:methanol (19:2)→ethyl acetate:methanol (1:1) as the eluant to afford [2-(t-butyldiphenylsilyloxy)ethyl]methylamine (2.67 g, yield 69%) as a transparent 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-e980fdf78319417e8e624bab196323da
Source dataset
uspto-grants-2006_02
Patent number
US07001897B2

Reaction notes

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