Methanol → Methyl 6,7,8,9-tetrahydropyrido[1,2-a]indole-1-carboxylate

HRID 2082318

反応式

HRID 2082318 の反応式
[CH:1]1[CH:9]=[CH:8][CH:7]=[C:6]2[C:2]=1[CH:3]=[C:4]1[CH2:13][CH2:12][CH2:11][CH2:10][N:5]12.[C:14](Cl)(Cl)=[O:15].[CH3:18][OH:19]>C(Cl)Cl.C1(C)C=CC=CC=1>[C:1]1([C:18]([O:15][CH3:14])=[O:19])[C:2]2[CH:3]=[C:4]3[CH2:13][CH2:12][CH2:11][CH2:10][N:5]3[C:6]=2[CH:7]=[CH:8][CH:9]=1

参加物

6

反応物 3

HCID 887MethanolHCID 6371PhosgeneHCID 108559426,7,8,9-Tetrahydropyrido[1,2-a]indole

生成物 1

HCID 19778122Methyl 6,7,8,9-tetrahydropyrido[1,2-a]indole-1-carboxylate収率 70.3%

試薬・触媒・溶媒 2

HCID 1140Toluene溶媒HCID 6344Dichloromethane溶媒

実験手順

6,7,8,9-tetrahydropyrido[1,2-a]indole (1.15 g, 6.7 mmol) in methylene chloride (5 ml) was added dropwise at 0° C. to a solution of phosgene (10 mmol) in toluene (5 ml). The reaction mixture was stirred for one hour after which methanol (1 ml) was added gradually and the mixture allowed to warm to ambient temperature. The solvent was removed under reduced pressure to yield a white solid. Recrystallization from hexane afforded 1.08 g (70.3% of methyl 6,7,8,9-tetrahydropyrido[1,2-a]indole-1-carboxylate, as white crystals, m.p. 102°-103° C. Anal. for C14H15NO2 : Calcd. C, 73.34; H, 6.59; N, 6.11. Found: C, 72.96; H, 6.61; N, 6.33.

後処理

  1. additionwas added gradually
  2. customThe solvent was removed under reduced pressure
  3. customto yield a white solid
  4. customRecrystallization from hexane

出典と根拠

ORDレコード
ord-ba37bc30eb764beab3f6b6c46c68ea25
出典データセット
uspto-grants-1993_02
特許番号
US05189041

関連ノート

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