Acetic Anhydride → N-acetyl 1-(2,2-diphenyleth-1-yl)-6,7-dimethoxy-1,2,3,4-tetrahydroisoquinoline

HRID 1071989노트

반응식

HRID 1071989 반응식
[C:1]1([CH:7]([C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)[CH2:8][CH:9]2[C:18]3[C:13](=[CH:14][C:15]([O:21][CH3:22])=[C:16]([O:19][CH3:20])[CH:17]=3)[CH2:12][CH2:11][NH:10]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C(N(CC)CC)C.[C:36](OC(=O)C)(=[O:38])[CH3:37]>C(Cl)Cl.CCOCC>[C:36]([N:10]1[CH2:11][CH2:12][C:13]2[C:18](=[CH:17][C:16]([O:19][CH3:20])=[C:15]([O:21][CH3:22])[CH:14]=2)[CH:9]1[CH2:8][CH:7]([C:1]1[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1)[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1)(=[O:38])[CH3:37]

참가 물질

6

반응물 3

HCID 7918Acetic AnhydrideHCID 8471TriethylamineHCID 223910171-(2,2-Diphenyleth-1-yl)-6,7-dimethoxy-1,2,3,4-tetrahydroisoquinoline

생성물 1

HCID 9909783N-acetyl 1-(2,2-diphenyleth-1-yl)-6,7-dimethoxy-1,2,3,4-tetrahydroisoquinoline수율 96%

시약·촉매·용매 2

HCID 3283Diethyl Ether용매HCID 6344Dichloromethane용매

실험 절차

A stirred solution of 1-(2,2-diphenyleth-1-yl)-6,7-dimethoxy-1,2,3,4-tetrahydroisoquinoline (1.8942 g, 5.0720 mmoles) in methylene chloride (15 mL) at 0° C. was treated with triethylamine (0.707 mL, 1.5 equiv.) and acetic anhydride (0.844 mL, 1.5 equiv.). After 2 hours at room temperature, The mixture was diluted with ether and washed with 1M sodium hydroxide (2×), water, and brine. The organic phase was dried over sodium sulfate and evaporated to give the product as a colorless foam (2.0178 g, 96%). 1H-NMR (CDCl3) δ (approx. 1.8:1 ratio of rotomers) 1.65 (rotomer A, s, 3H), 1.96 (rotomer B, s, 3H), 2.35 (rotomer B, m, 1H), 2.54 (rotomer A, m, 1H), 2.67 (rotomer A, m, 1H), 2.80 (rotomers A & B, m, 1H), 2.94 (rotomer A, m, 1H), 3.21 (rotomer A, m, 1H), 3.43 (rotomers A & B, m, 1H), 3.77 (rotomer B, s, 3H), 3.88 (rotomers A & B, s, 3H), 3.92 (rotomer A, s, 3H), 4.03 (rotomer A, m, 1H), 4.12 (rotomer B, t, 1H), 4.60 (rotomer B, m, 1H), 5.68 (rotomer A, m, 1H), 6.38 (rotomer B, s, 1H), 6.53 (rotomer A, s, 1H), 6.60 (rotomer B, s, 1H), 6.62 (rotomer A, s, 1H), 7.32 (rotomers A & B, m, 10H). Mass spec. 416.4 (MH)+. Anal. Calc. for C27H29NO3-2/3H2O: C-75.85, H-7.15, N-3.28. Found: C-75.89, H-7.03, N-3.24.

후처리

  1. washwashed with 1M sodium hydroxide (2×), water, and brine
  2. dry with materialThe organic phase was dried over sodium sulfate
  3. customevaporated

출처 및 근거

ORD 기록
ord-dd3be0205a8343068aa8d5c70eec4ef9
출처 데이터셋
uspto-grants-2005_06
특허 번호
US06908931B2

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