[2-(t-Butyldiphenylsilyloxy)ethyl]carbamic acid benzyl ester → 2-(t-Butyldiphenylsilyloxy)ethylamine

HRID 891625Notes

Reaction equation

HRID 891625 reaction equation
C(OC(=O)[NH:10][CH2:11][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.[OH-].[OH-].[Pd+2]>[Si:14]([O:13][CH2:12][CH2:11][NH2:10])([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]=1

Participants

4

Reactant 1

HCID 16221537[2-(t-Butyldiphenylsilyloxy)ethyl]carbamic acid benzyl ester

Product 1

HCID 110010432-(t-Butyldiphenylsilyloxy)ethylamineYield 72.1%

Reagents, catalysts & solvents 2

HCID 9942167Palladium hydroxideCatalystHCID 887MethanolSolvent

Procedure

A solution of [2-(t-butyldiphenylsilyloxy)ethyl]carbamic acid benzyl ester (3.01 g, 6.9 mmol) (obtained as described in Reference Example 33(1)) in methanol (150 ml) was subjected to catalytic hydrogenation in the presence of 20% palladium hydroxide on charcoal (3.0 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 methylene chloride:methanol (10:1) as the eluant to afford 2-(t-butyldiphenylsilyloxy)ethylamine (1.49 g, yield 72%) as a pale brown syrup.

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-8bcababc24424e45b23036004945c6c9
Source dataset
uspto-grants-2006_02
Patent number
US07001897B2

Reaction notes

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