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

HRID 396723노트

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HRID 396723 반응식
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]

참가 물질

6

반응물 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

생성물 1

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

시약·촉매·용매 2

HCID 9942167Palladium hydroxide촉매HCID 702Ethanol용매

실험 절차

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+).

후처리

  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)

출처 및 근거

ORD 기록
ord-b0361dfc6ae84cdeae06d1be88c96338
출처 데이터셋
uspto-grants-2003_08
특허 번호
US06608084B1

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