Homoveratrylamine → 1-(2,2-Diphenyleth-1-yl)-6,7-dimethoxy-1,2,3,4-tetrahydroisoquinoline

HRID 1071986노트

반응식

HRID 1071986 반응식
[C:1]1([CH:7]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)[CH2:8][CH:9]=O)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH3:17][O:18][C:19]1[CH:20]=[C:21]([CH2:27][CH2:28][NH2:29])[CH:22]=[CH:23][C:24]=1[O:25][CH3:26]>C(O)=O>[C:1]1([CH:7]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)[CH2:8][CH:9]2[C:22]3[C:21](=[CH:20][C:19]([O:18][CH3:17])=[C:24]([O:25][CH3:26])[CH:23]=3)[CH2:27][CH2:28][NH:29]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

참가 물질

4

반응물 2

HCID 8421HomoveratrylamineHCID 110746643,3-Diphenylpropanal

생성물 1

HCID 223910171-(2,2-Diphenyleth-1-yl)-6,7-dimethoxy-1,2,3,4-tetrahydroisoquinoline

시약·촉매·용매 1

HCID 284Formic Acid용매

실험 절차

A solution of 3,3-diphenylpropionaldehyde (19.25 g, 91.54 mmoles) and 2-(3,4-dimethoxyphenyl)ethylamine (16.59 g, 1 equiv.) in 90% formic acid 125 mL) was heated at 95° C. for 16 hours. Upon cooling to room temperature, the solvent was removed on the rotary evaporator, and the residue was partitioned between ethyl acetate and 1M sodium hydroxide. The organic phase was washed with 1M sodium hydroxide and brine, dried over sodium sulfate, and evaporated to give a thick gum. The product was purified by flash chromatography on silica gel, eluting with 20:1 ethyl acetate/methanol, to give a thick gum that solidified upon standing (17.01 g, 50%). 1H-NMR (CDCl3) δ 2.42 (m, 1H), 2.53 (m, 1H), 2.67 (m, 2H), 2.98 (m, 1H), 3.18 (m, 1H), 3.77 (ABq, 1H), 3.84 and 3.88 (s, each 3H), 4.48 (ABq, 1H), 6.46 and 6.57 (s, each 1H), 7.32 (m, 10 H). Mass spec. 374.2 (MH)+.

후처리

  1. customthe solvent was removed on the rotary evaporator
  2. customthe residue was partitioned between ethyl acetate and 1M sodium hydroxide
  3. washThe organic phase was washed with 1M sodium hydroxide and brine
  4. dry with materialdried over sodium sulfate
  5. customevaporated
  6. customto give a thick gum
  7. customThe product was purified by flash chromatography on silica gel
  8. washeluting with 20:1 ethyl acetate/methanol
  9. customto give a thick gum that

출처 및 근거

ORD 기록
ord-e520eef60b3d4d86b686089b2a7800d7
출처 데이터셋
uspto-grants-2005_06
특허 번호
US06908931B2

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