Acetic Acid → Methyl 3-Amino-3-(1-boc-1,2,3,4-tetrahydro-quinolin-6-yl)-propionate

HRID 396723Notes

Reaction equation

HRID 396723 reaction equation
C([N:8]([C@H](C1C=CC=CC=1)C)[C@@H:9]([C:15]1[CH:16]=[C:17]2[C:22](=[CH:23][CH:24]=1)[N:21]([C:25]([O:27][C:28]([CH3:31])([CH3:30])[CH3:29])=[O:26])[CH2:20][CH2:19][CH2:18]2)[CH2:10][C:11]([O:13][CH3:14])=[O:12])C1C=CC=CC=1.C(O)(=O)C.O>C(O)C.[OH-].[OH-].[Pd+2]>[NH2:8][CH:9]([C:15]1[CH:16]=[C:17]2[C:22](=[CH:23][CH:24]=1)[N:21]([C:25]([O:27][C:28]([CH3:31])([CH3:30])[CH3:29])=[O:26])[CH2:20][CH2:19][CH2:18]2)[CH2:10][C:11]([O:13][CH3:14])=[O:12]

Participants

6

Reactant 3

HCID 176Acetic AcidHCID 962WaterHCID 21354704methyl 3-{R}-[benzyl-({S}-1-phenyl-ethyl)-amino]-3-(1-boc-1,2,3,4-tetrahydro-quinolin-6-yl)-propionate

Product 1

HCID 23003972Methyl 3-Amino-3-(1-boc-1,2,3,4-tetrahydro-quinolin-6-yl)-propionateYield 41.3%

Reagents, catalysts & solvents 2

HCID 9942167Palladium hydroxideCatalystHCID 702EthanolSolvent

Procedure

A solution of methyl 3-{R}-[benzyl-({S}-1-phenyl-ethyl)-amino]-3-(1-boc-1,2,3,4-tetrahydro-quinolin-6-yl)-propionate (6.5 g, Reference Example 15) in ethanol (100 ml) was treated with 20% palladium hydroxide on charcoal (1.0 g), acetic acid (3.6 ml) and water (10 ml) and the mixture was hydrogenated at room temperature overnight. The spent catalyst was removed by filtration through Celite and the filtrate was evaporated to low bulk. The residue was taken up in ether and this solution was washed with aqueous sodium bicarbonate solution, and the layers separated. The aqueous layer was extracted twice with fresh ether and the combined ether extracts were washed with brine, then dried and then evaporated. The residue was subjected to flash chromatography on silica eluting with a mixture of methanol and dichloromethane (1:9, v/v) to give the title compound (1.7 g) as a clear oil which slowly crystallised on standing. MS (ES+) 335 (MH+), 357 (MNa+), 669 (2MH+).

Workup

  1. customThe spent catalyst was removed by filtration through Celite
  2. customthe filtrate was evaporated to low bulk
  3. washthis solution was washed with aqueous sodium bicarbonate solution
  4. customthe layers separated
  5. extractionThe aqueous layer was extracted twice with fresh ether
  6. washthe combined ether extracts were washed with brine
  7. customdried
  8. customevaporated
  9. additionThe residue was subjected to flash chromatography on silica eluting with a mixture of methanol and dichloromethane (1:9, v/v)

Sources & evidence

ORD record
ord-b0361dfc6ae84cdeae06d1be88c96338
Source dataset
uspto-grants-2003_08
Patent number
US06608084B1

Reaction notes

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