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

HRID 2294362Notes

Reaction equation

HRID 2294362 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-82564c498cf74d7b8f07f74a5384ed02
Source dataset
uspto-grants-1997_11
Patent number
US05688823

Reaction notes

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