Benzyl N-[2-t-Butyldimethylsilyloxy-1,1-dimethylethyl]carbamate → 2-tert-Butyldimethylsilyloxy-1,1-dimethylethylamine

HRID 1901748Notes

Reaction equation

HRID 1901748 reaction equation
[Si:1]([O:8][CH2:9][C:10]([NH:13]C(=O)OCC1C=CC=CC=1)([CH3:12])[CH3:11])([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2]>[Pd].C(O)C>[Si:1]([O:8][CH2:9][C:10]([NH2:13])([CH3:12])[CH3:11])([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2]

Participants

4

Reactant 1

HCID 21474722Benzyl N-[2-t-Butyldimethylsilyloxy-1,1-dimethylethyl]carbamate

Product 1

HCID 148067402-tert-Butyldimethylsilyloxy-1,1-dimethylethylamineYield 83.4%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A procedure similar to that described in Preparation 9 was repeated, except that 8.00 g of benzyl N-[2-t-butyldimethylsilyloxy-1,1-dimethylethyl]carbamate (prepared as described in Preparation 103), 1.60 g of 10% w/w palladium-on-carbon and 80 ml of ethanol were used, to give 4.02 g of the title compound having an Rf value of 0.14 (on silica gel thin layer chromatography, using ethyl acetate as the eluent).

Workup

  1. customA procedure similar to that described in Preparation 9

Sources & evidence

ORD record
ord-0c046745f5414763b8b2f9678882e764
Source dataset
uspto-grants-1996_11
Patent number
US05578620

Reaction notes

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