tert-butyl (3R)-3-{benzyl[(1R)-1-phenylethyl]amino}heptanoate → tert-butyl (3R)-3-aminoheptanoate

HRID 64405Notes

Reaction equation

HRID 64405 reaction equation
C([N:8]([C@@H](C1C=CC=CC=1)C)[C@H:9]([CH2:18][CH2:19][CH2:20][CH3:21])[CH2:10][C:11]([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:12])C1C=CC=CC=1>CO.[C].[Pd]>[NH2:8][C@H:9]([CH2:18][CH2:19][CH2:20][CH3:21])[CH2:10][C:11]([O:13][C:14]([CH3:15])([CH3:16])[CH3:17])=[O:12]

Participants

4

Reactant 1

HCID 86713413tert-butyl (3R)-3-{benzyl[(1R)-1-phenylethyl]amino}heptanoate

Product 1

HCID 86713412tert-butyl (3R)-3-aminoheptanoateYield 78.6%

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 887MethanolSolvent

Procedure

To a solution of 1.15 g of tert-butyl (3R)-3-{benzyl[(1R)-1-phenylethyl]amino}heptanoate in 30 ml of methanol was added 450 mg of 10% palladium-carbon, followed by stirring overnight under a hydrogen atmosphere at 4 atm. The reaction mixture was filtered over Celite and the solvent was then evaporated under reduced pressure. The obtained residue was purified by silica gel column chromatography to obtain 460 mg of tert-butyl (3R)-3-aminoheptanoate.

Workup

  1. filtrationThe reaction mixture was filtered over Celite
  2. customthe solvent was then evaporated under reduced pressure
  3. customThe obtained residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-d166927b3c2e44feaa18d7ebbda2a906
Source dataset
uspto-grants-2016_09
Patent number
US09447090B2

Reaction notes

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