Chloroform → (-)-Acetic acid cis-4-benzyloxy-cyclopent-2-enyl ester

HRID 2555

반응식

HRID 2555 반응식
[CH2:1]([O:8][C@@H:9]1[CH2:13][C@H:12]([OH:14])[CH:11]=[CH:10]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(N(CC)CC)C.[C:22]([O:25][CH:26]=[CH2:27])(=[O:24])[CH3:23].C(Cl)(Cl)Cl>COC(C)(C)C>[CH2:1]([O:8][C@@H:9]1[CH2:13][C@H:12]([OH:14])[CH:11]=[CH:10]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH2:1]([O:8][C@@H:9]1[CH2:13][C@H:26]([O:25][C:22](=[O:24])[CH3:23])[CH:27]=[CH:10]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

참가 물질

7

반응물 4

HCID 6212Chloroform2회HCID 7904Vinyl AcetateHCID 8471TriethylamineHCID 15812323(1S,4R)-4-(Benzyloxy)cyclopent-2-en-1-ol

생성물 2

HCID 15812323(1S,4R)-4-(Benzyloxy)cyclopent-2-en-1-ol수율 29%HCID 86752290(-)-Acetic acid cis-4-benzyloxy-cyclopent-2-enyl ester수율 70%

시약·촉매·용매 1

HCID 15413tert-Butyl methyl ether용매

실험 절차

Cis-4-benzyloxy-cyclopent-2-enol (500 mg, prepared in example 16) is dissolved in tert-butyl methyl ether (8.6 mL, anhydrous). To the solution is added triethylamine (0.7 eq), pancreatin (3 wt eq, available from Sigma Chemical Company), and vinyl acetate (5 eq). The reaction is allowed to stir for 7 hours at room temperature. The reaction is then filtered through diatomaceous earth and the filtrate is concentrated under vacuum. The products are separated by chromatography on silica gel (20% ethyl acetate/hexane) to provide (-)-cis-4-benzyloxy-cyclopent-2-enol (A) (147 mg, 29% yield) [α]20D -12°, (c=1.09, chloroform), and (-)-acetic acid cis-4-benzyloxy-cyclopent-2-enyl ester (B) (427 mg, 70% yield),[α]20D =-5.2°, (c=0.97, chloroform), 1 H NMR (CDCl3) δ 7.3 (m, 5H), 6.13 (d, 1H, J=5 Hz), 5.99 (d, 1H, J=5 Hz), 5.5 (m, 1H), 4.59 (d, 1H, J=11.8 Hz), 4.54 (d, 1H, J=11.8 Hz), 4.5 (m, 1H), 2.78 (d appt, 1H, J=7.2, 14.3 Hz), 2.05 (s, 3H), 1.76 (d appt, 1H, J=4.4, 14.3 Hz); 13C NMR (CDCl3) δ171.1, 138.5, 136.4, 133.1, 128.7, 128, 127.9, 81.4, 77.1, 71.2, 37.8, 21.4.

후처리

  1. filtrationThe reaction is then filtered through diatomaceous earth
  2. concentrationthe filtrate is concentrated under vacuum
  3. customThe products are separated by chromatography on silica gel (20% ethyl acetate/hexane)

출처 및 근거

ORD 기록
ord-443e36063c0a47edae71957a9c2af350
출처 데이터셋
uspto-grants-1998_03
특허 번호
US05728899

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