Triethylamine → (3aR,7aR)-7,7-diphenyl-2-[(S)-2-phenylpropionyl]-4-perhydroisoindolone

HRID 1029918노트

반응식

HRID 1029918 반응식
[C:1]1([C@H:7]([CH3:11])[C:8]([OH:10])=O)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.Cl.[C:13]1([C:19]2([C:29]3[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=3)[C@H:27]3[C@H:23]([CH2:24][NH:25][CH2:26]3)[C:22](=[O:28])[CH2:21][CH2:20]2)[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.C(N(CC)CC)C>ClCCl>[C:29]1([C:19]2([C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=3)[C@H:27]3[C@H:23]([CH2:24][N:25]([C:8](=[O:10])[C@H:7]([C:1]4[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=4)[CH3:11])[CH2:26]3)[C:22](=[O:28])[CH2:21][CH2:20]2)[CH:30]=[CH:31][CH:32]=[CH:33][CH:34]=1

참가 물질

5

반응물 3

HCID 8471TriethylamineHCID 27246222-Phenylpropionic acid, (+)-HCID 22843247(3aR,7aR)-7,7-diphenyl-4-perhydroisoindolone hydrochloride

생성물 1

HCID 22843246(3aR,7aR)-7,7-diphenyl-2-[(S)-2-phenylpropionyl]-4-perhydroisoindolone수율 57.3%

시약·촉매·용매 1

HCID 6344Dichloromethane용매2회

실험 절차

N,N'-Carbonyldiimidazole (0.66 g) is added to a solution of (S)-2-phenylpropionic acid (0.62 g) in dry dichloromethane (30 cc), cooled to +5° C. The mixture is stirred for 40 minutes at +5° C. and a solution of (3aR,7aR)-7,7-diphenyl-4-perhydroisoindolone hydrochloride (1.35 g) and triethylamine (0.57 cc) in dichloromethane (40 cc) is then added. The reaction mixture is stirred at 20° C. for 16 hours, then washed with distilled water (2×50 cc), dried over magnesium sulphate and filtered and the filtrate is concentrated to dryness under reduced pressure (2.7 kPa). The residue is chromatographed on a silica gel column (0.2-0.063 mm, diameter 1.8 cm, height 15 cm), eluting with ethyl acetate and collecting 15 cc fractions. The first fraction is concentrated to dryness under reduced pressure (2.7 kPa). (3aR,7aR)-7,7-diphenyl-2-[(S)-2-phenylpropionyl]-4-perhydroisoindolone (1 g) is obtained in the form of a white meringue. [α]D20 =-231° (c=1, methanol).

후처리

  1. temperaturecooled to +5° C
  2. stirringThe reaction mixture is stirred at 20° C. for 16 hours
  3. washwashed with distilled water (2×50 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 residue is chromatographed on a silica gel column (0.2-0.063 mm, diameter 1.8 cm, height 15 cm)
  8. washeluting with ethyl acetate
  9. customcollecting 15 cc fractions
  10. concentrationThe first fraction is concentrated to dryness under reduced pressure (2.7 kPa)

출처 및 근거

ORD 기록
ord-8fdfe51c68b741059dc6b8e8124d23f3
출처 데이터셋
uspto-grants-1992_04
특허 번호
US05102667

반응 노트

불러오는 중…