ethyl 2-(N-benzylaminomethyl)-3-t-butyldimethylsilyloxybutanoate → Ethyl 2-aminomethyl-3-t-butyldimethylsilyloxybutanoate

HRID 1975457Notes

Reaction equation

HRID 1975457 reaction equation
C([NH:8][CH2:9][CH:10]([CH:16]([O:18][Si:19]([C:22]([CH3:25])([CH3:24])[CH3:23])([CH3:21])[CH3:20])[CH3:17])[C:11]([O:13][CH2:14][CH3:15])=[O:12])C1C=CC=CC=1.[H][H]>CO.[Pd]>[NH2:8][CH2:9][CH:10]([CH:16]([O:18][Si:19]([C:22]([CH3:24])([CH3:23])[CH3:25])([CH3:21])[CH3:20])[CH3:17])[C:11]([O:13][CH2:14][CH3:15])=[O:12]

Participants

5

Reactant 2

HCID 19099345ethyl 2-(N-benzylaminomethyl)-3-t-butyldimethylsilyloxybutanoateHCID 178418361HCID 178418361, compound

Product 1

HCID 19099249Ethyl 2-aminomethyl-3-t-butyldimethylsilyloxybutanoateYield 95.1%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

To a solution of 70.2 g of ethyl 2-(N-benzylaminomethyl)-3-t-butyldimethylsilyloxybutanoate in methanol (100 ml) was added portionwise 10.0 g of 10% wet palladium on carbon under nitrogen atmosphere. The mixture was shaken vigorously under 3.5 atmospheric pressure of hydrogen. After 8 hours, palladium on carbon was filtered off and washed with chloroform. The filtrate was evaporated to dryness under reduced pressure to give 50.3 g of crude ethyl 2-aminomethyl-3-t-butyldimethylsilyloxybutanoate.

Workup

  1. filtrationpalladium on carbon was filtered off
  2. washwashed with chloroform
  3. customThe filtrate was evaporated to dryness under reduced pressure

Sources & evidence

ORD record
ord-715b28ce1ee246ee92e94d197a9b08d5
Source dataset
uspto-grants-1994_02
Patent number
US05286721

Reaction notes

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