Phenylacetyl chloride → (3aR,7aR)-7,7-Diphenyl-2-(phenylacetyl)perhydro-4-isoindolone

HRID 1196267노트

반응식

HRID 1196267 반응식
[C:1]1([CH2:7][C:8](Cl)=[O:9])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C(N(CC)CC)C.Cl.[C:19]1([C:25]2([C:35]3[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=3)[C@H:33]3[C@H:29]([CH2:30][NH:31][CH2:32]3)[C:28](=[O:34])[CH2:27][CH2:26]2)[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1.C(=O)([O-])O.[Na+]>ClCCl>[C:35]1([C:25]2([C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=3)[C@H:33]3[C@H:29]([CH2:30][N:31]([C:8](=[O:9])[CH2:7][C:1]4[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=4)[CH2:32]3)[C:28](=[O:34])[CH2:27][CH2:26]2)[CH:36]=[CH:37][CH:38]=[CH:39][CH:40]=1

참가 물질

6

반응물 4

HCID 7679Phenylacetyl chlorideHCID 8471TriethylamineHCID 516892Sodium BicarbonateHCID 22843247(3aR,7aR)-7,7-diphenyl-4-perhydroisoindolone hydrochloride

생성물 1

HCID 22843240(3aR,7aR)-7,7-Diphenyl-2-(phenylacetyl)perhydro-4-isoindolone

시약·촉매·용매 1

HCID 6344Dichloromethane용매2회

실험 절차

A solution of phenylacetyl chloride (4 cc) and triethylamine (8.6 cc) in dichloromethane (10 cc) is added dropwise to a solution, cooled to +5° C., of (3aR,7aR)-7,7-diphenylperhydro-4-isoindolone hydrochloride (10 g) in dry dichloromethane (80 cc). The reaction mixture is stirred for 2 hours at +5° C. and then for 20 hours at 20° C. The reaction mixture is treated with saturated aqueous sodium hydrogen carbonate solution (30 cc); the organic phase is washed with distilled water (2×50 cc), dried over magnesium sulphate, filtered and concentrated to dryness under reduced pressure (2.7 kPa). The residue is crystallized in acetonitrile (15 cc). The crystals are drained, washed with acetonitrile (10 cc) and with isopropyl ether (10 cc) and dried. (3aR,7aR)-7,7-Diphenyl-2-(phenylacetyl)perhydro-4-isoindolone (5.7 g), m.p. 173° C. is obtained; [α]D20 =-282° (c=1, methanol).

후처리

  1. waitfor 20 hours at 20° C
  2. washthe organic phase is washed with distilled water (2×50 cc)
  3. dry with materialdried over magnesium sulphate
  4. filtrationfiltered
  5. concentrationconcentrated to dryness under reduced pressure (2.7 kPa)
  6. customThe residue is crystallized in acetonitrile (15 cc)
  7. washwashed with acetonitrile (10 cc) and with isopropyl ether (10 cc)
  8. customdried

출처 및 근거

ORD 기록
ord-8ebe565242554887a4be77d6e37a78d5
출처 데이터셋
uspto-grants-1992_05
특허 번호
US05112988

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