Acetic Anhydride → trans-3-(3-Cyclopentoxy-4-methoxyphenyl)-4-methoxycarbonyl-1-(methylcarbonyl)pyrrolidine

HRID 1377766노트

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HRID 1377766 반응식
[CH:1]1([O:6][C:7]2[CH:8]=[C:9]([C@H:15]3[C@H:19]([C:20]([O:22][CH3:23])=[O:21])[CH2:18][NH:17][CH2:16]3)[CH:10]=[CH:11][C:12]=2[O:13][CH3:14])[CH2:5][CH2:4][CH2:3][CH2:2]1.[C:24](OC(=O)C)(=[O:26])[CH3:25]>C(Cl)Cl.CN(C)C1C=CN=CC=1>[CH:1]1([O:6][C:7]2[CH:8]=[C:9]([C@H:15]3[C@H:19]([C:20]([O:22][CH3:23])=[O:21])[CH2:18][N:17]([C:24]([CH3:25])=[O:26])[CH2:16]3)[CH:10]=[CH:11][C:12]=2[O:13][CH3:14])[CH2:2][CH2:3][CH2:4][CH2:5]1

참가 물질

5

반응물 2

HCID 7918Acetic AnhydrideHCID 70093357trans-3-(3-Cyclopentoxy-4-methoxyphenyl)-4-(methoxycarbonyl)pyrrolidine

생성물 1

HCID 67015228trans-3-(3-Cyclopentoxy-4-methoxyphenyl)-4-methoxycarbonyl-1-(methylcarbonyl)pyrrolidine수율 54%

시약·촉매·용매 2

HCID 142844-(Dimethylamino)pyridine촉매HCID 6344Dichloromethane용매2회

실험 절차

To a solution of trans-3-(3-cyclopentoxy-4-methoxyphenyl)-4-(methoxycarbonyl)pyrrolidine (605 mg, 1.89 mmol) in 5 mL of CH2Cl2 was added 4-dimethylaminopyridine (347 mg, 2.84 mmol), followed by 1 mL of acetic anhydride After 12 hr the reaction was diluted with CH2Cl2 and washed with 1M H3PO4. The organic layer was dried over MgSO4, filtered, and concentrated under reduced pressure. Silica gel chromatography (2:1, hexanes:ethyl acetate) provided trans-3-(3-cyclopentoxy-4-methoxyphenyl)-4-methoxycarbonyl-1-(methylcarbonyl)pyrrolidine as a viscous oil (370 mg, 54%). 1H-NMR (300 MHz) analysis indicates a 1:1 mixture of amide rotamers (δ 2.07 and 2.09 singlets). Anal. Calcd for C20H27NO5 : C, 66.46; H, 7.53; N, 3.88. Found: C, 66.19; H, 7.58; N, 3.82.

후처리

  1. washwashed with 1M H3PO4
  2. dry with materialThe organic layer was dried over MgSO4
  3. filtrationfiltered
  4. concentrationconcentrated under reduced pressure

출처 및 근거

ORD 기록
ord-eafbcf093f8340f2b19fcd86ac8da52b
출처 데이터셋
uspto-grants-1997_09
특허 번호
US05665754

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