tert-butyl(3S)-3-{[(benzyloxy)carbonyl]amino}-4-(methoxymethoxy)butanoate → Tert-butyl(3s)-3-amino-4-(methoxymethoxy)butanoate

HRID 1374430Notes

Reaction equation

HRID 1374430 reaction equation
C(OC([NH:11][C@H:12]([CH2:21][O:22][CH2:23][O:24][CH3:25])[CH2:13][C:14]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15])=O)C1C=CC=CC=1.[H][H]>CO.[Pd]>[NH2:11][C@H:12]([CH2:21][O:22][CH2:23][O:24][CH3:25])[CH2:13][C:14]([O:16][C:17]([CH3:20])([CH3:18])[CH3:19])=[O:15]

Participants

5

Reactant 2

HCID 69350141tert-butyl(3S)-3-{[(benzyloxy)carbonyl]amino}-4-(methoxymethoxy)butanoateHCID 178418361HCID 178418361, compound

Product 1

HCID 58781940Tert-butyl(3s)-3-amino-4-(methoxymethoxy)butanoateYield 84%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalyst2×HCID 887MethanolSolvent

Procedure

To a solution of tert-butyl(3S)-3-{[(benzyloxy)carbonyl]amino}-4-(methoxymethoxy)butanoate (16.3 g, 53 mmol) in methanol (150 ml) was added 10% Pd—C (3.3 g) and the mixture was stirred for 6 hours at a hydrogen atmosphere. Additional 10% Pd—C (0.75 g) was added thereto and the mixture was stirred for 1.5 hours. After removal of catalyst by filtration, the solvent was removed in vacuo to give tert-butyl(3S)-3-amino-4-(methoxymethoxy)butanoate (9.7 g, 84%).

Workup

  1. customAfter removal of catalyst
  2. filtrationby filtration
  3. customthe solvent was removed in vacuo

Sources & evidence

ORD record
ord-2a4ac2b220d945b0a45e919cde49af99
Source dataset
uspto-grants-2007_01
Patent number
US07163936B2

Reaction notes

Loading…