Triethylamine → (3aRS,7aRS)-7,7-diphenyl-2-[(3-(trifluoromethyl)phenyl)acetyl]-4-perhydroisoindolone

HRID 1029885

반응식

HRID 1029885 반응식
[F:1][C:2]([F:14])([F:13])[C:3]1[CH:4]=[C:5]([CH2:9][C:10]([OH:12])=O)[CH:6]=[CH:7][CH:8]=1.Cl.[C:16]1([C:22]2([C:32]3[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=3)[CH:30]3[CH:26]([CH2:27][NH:28][CH2:29]3)[C:25](=[O:31])[CH2:24][CH2:23]2)[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1.C(N(CC)CC)C>ClCCl>[C:32]1([C:22]2([C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=3)[CH:30]3[CH:26]([CH2:27][N:28]([C:10](=[O:12])[CH2:9][C:5]4[CH:6]=[CH:7][CH:8]=[C:3]([C:2]([F:1])([F:14])[F:13])[CH:4]=4)[CH2:29]3)[C:25](=[O:31])[CH2:24][CH2:23]2)[CH:33]=[CH:34][CH:35]=[CH:36][CH:37]=1

참가 물질

5

반응물 3

HCID 8471TriethylamineHCID 676953-(Trifluoromethyl)benzeneacetic acidHCID 212645437,7-Diphenylhexahydro-1H-isoindol-4(2H)-one hydrochloride

생성물 1

HCID 67915869(3aRS,7aRS)-7,7-diphenyl-2-[(3-(trifluoromethyl)phenyl)acetyl]-4-perhydroisoindolone수율 60.2%

시약·촉매·용매 1

HCID 6344Dichloromethane용매2회

실험 절차

N,N'-Carbonyldiimidazole (1.13 g) is added to a solution of 3-(trifluoromethyl)phenylacetic acid (1.43 g) in dry dichloromethane (30 cc), cooled to +5° C. The mixture is stirred for 15 minutes at +5° C. and a solution of (3aRS,7aRS)-7,7-diphenyl-4-perhydroisoindolone hydrochloride (2.28 g) and triethylamine (1.96 cc) in dichloromethane (20 cc) is then added. The reaction mixture is stirred at 20° C. for 2 hours, then washed with water (2×150 cc), dried over magnesium sulphate and filtered and the filtrate is concentrated to dryness under reduced pressure (2.7 kPa). The meringue obtained is crystallized from a mixture of acetonitrile (30 cc) and isopropyl ether (30 cc). The crystals are drained, washed with isopropyl ether and dried. (3aRS,7aRS)-7,7-diphenyl-2-[(3-(trifluoromethyl)phenyl)acetyl]-4-perhydroisoindolone (2 g) is obtained in the form of white crystals melting at 184° C.

후처리

  1. temperaturecooled to +5° C
  2. stirringThe reaction mixture is stirred at 20° C. for 2 hours
  3. washwashed with water (2×150 cc)
  4. dry with materialdried over magnesium sulphate
  5. filtrationfiltered
  6. concentrationthe filtrate is concentrated to dryness under reduced pressure (2.7 kPa)
  7. customThe meringue obtained
  8. customis crystallized from a mixture of acetonitrile (30 cc) and isopropyl ether (30 cc)
  9. washwashed with isopropyl ether
  10. customdried

출처 및 근거

ORD 기록
ord-bb64d478185c43cfb58db2be6b720304
출처 데이터셋
uspto-grants-1992_04
특허 번호
US05102667

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