(+/-)-trans-2-Cyclopropylmethyl-4a-(3-methoxyphenyl)-6-oxo-1,2,3,4,4a,5,6,7,8,8a-decahydroisoquinoline hydrochloride → (+/-)-trans-6-Cyclopropylmethyl-2-diethylaminocarbonyl-8a-(3-methoxyphenyl)-3-methyl-4,4a,5,6,7,8,8a,9-octahydro-1H-pyrrolo[2,3-g]isoquinoline hydrochloride

HRID 2871

반응식

HRID 2871 반응식
[ClH:1].[CH:2]1([CH2:5][N:6]2[CH2:15][CH2:14][C@@:13]3([C:16]4[CH:21]=[CH:20][CH:19]=[C:18]([O:22][CH3:23])[CH:17]=4)[C@@H:8]([CH2:9][CH2:10][C:11](=O)[CH2:12]3)[CH2:7]2)[CH2:4][CH2:3]1.[CH2:25]([N:27]([CH2:42][CH3:43])[C:28](=[O:41])[C:29](=[N:33]NC1C=CC=CC=1)[C:30](=O)[CH3:31])[CH3:26].CC(O[Na])=O>[Zn].C(O)(=O)C>[ClH:1].[CH:2]1([CH2:5][N:6]2[CH2:15][CH2:14][C@:13]3([C:16]4[CH:21]=[CH:20][CH:19]=[C:18]([O:22][CH3:23])[CH:17]=4)[C@H:8]([CH2:9][C:10]4[C:30]([CH3:31])=[C:29]([C:28]([N:27]([CH2:42][CH3:43])[CH2:25][CH3:26])=[O:41])[NH:33][C:11]=4[CH2:12]3)[CH2:7]2)[CH2:4][CH2:3]1

참가 물질

6

반응물 3

HCID 86752322(+/-)-trans-2-Cyclopropylmethyl-4a-(3-methoxyphenyl)-6-oxo-1,2,3,4,4a,5,6,7,8,8a-decahydroisoquinoline hydrochlorideHCID 178418240HCID 178418240, 화합물HCID 178418247HCID 178418247, 화합물

생성물 1

HCID 22883672(+/-)-trans-6-Cyclopropylmethyl-2-diethylaminocarbonyl-8a-(3-methoxyphenyl)-3-methyl-4,4a,5,6,7,8,8a,9-octahydro-1H-pyrrolo[2,3-g]isoquinoline hydrochloride수율 57.9%

시약·촉매·용매 2

HCID 23994Zinc촉매HCID 176Acetic Acid용매

실험 절차

0.28 g (0.80 mmol) of (±)-trans-2-cyclopropylmethyl-4a-(3-methoxyphenyl)-6-oxo-1,2,3,4,4a,5,6,7,8,8a-decahydroisoquinoline hydrochloride, 0.56 g (2.14 mmol) of N,N-diethyl-2-phenylhydrazono-3-oxobutyramide, 0.131 g (1.6 mmol) of CH3COONa, 0.402 g (6.16 mmol) of zinc dust and 10 ml of glacial acetic acid were treated as described in example 1. The residue was purified by flash chromatography ((i-Pr)2O/MeOH/conc. NH4OH 90:10:0.5). The product was dissolved in acetone and the solution brought to acidic pH with Et2O/HCl . The solid was filtered, washed and dried yielding 0.225 g of the title compound. M.p.=190°-195° C.

후처리

  1. customThe residue was purified by flash chromatography ((i-Pr)2O/MeOH/conc. NH4OH 90:10:0.5)
  2. dissolutionThe product was dissolved in acetone
  3. filtrationThe solid was filtered
  4. washwashed
  5. customdried

출처 및 근거

ORD 기록
ord-aadff68fc9964d3da32320a270554fa5
출처 데이터셋
uspto-grants-1998_03
특허 번호
US05731322

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