Water → 1-[2-(Chroman-3-yl)ethyl]-1,2,5,6-tetrahydropyridine-3-carboxylic acid methyl ester hydrochloride

HRID 1032420ノート

反応式

HRID 1032420 の反応式
[BH4-].[Na+].C1(C)C=CC(S([O-])(=O)=O)=CC=1.[O:14]1[C:23]2[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=2)[CH2:17][CH:16]([CH2:24][CH2:25][N+:26]2[CH:31]=[CH:30][CH:29]=[C:28]([C:32]([O:34][CH3:35])=[O:33])[CH:27]=2)[CH2:15]1.O.[Cl:37]CCl>CO>[ClH:37].[CH3:35][O:34][C:32]([C:28]1[CH2:27][N:26]([CH2:25][CH2:24][CH:16]2[CH2:17][C:18]3[C:23](=[CH:22][CH:21]=[CH:20][CH:19]=3)[O:14][CH2:15]2)[CH2:31][CH2:30][CH:29]=1)=[O:33]

参加物

6

反応物 4

HCID 962WaterHCID 6344Dichloromethane2 回HCID 4311764Sodium borohydrideHCID 148384541-[2-(Chroman-3-yl)ethyl]-3-methoxycarbonylpyridinium p-toluenesulphonate

生成物 1

HCID 679071351-[2-(Chroman-3-yl)ethyl]-1,2,5,6-tetrahydropyridine-3-carboxylic acid methyl ester hydrochloride

試薬・触媒・溶媒 1

HCID 887Methanol溶媒

実験手順

At -10° and while stirring, 1.41 g of sodium borohydride are introduced within a period of 90 minutes into a suspension of 8.45 g (18 mmol) of 1-[2-(chroman-3-yl)ethyl]-3-methoxycarbonylpyridinium p-toluenesulphonate in 43 ml of methanol. Stirring is continued for 1 hour at 0° and for 2 hours at room temperature and then 50 ml of water are added to the reaction mixture and extraction by shaking is carried out twice with 100 ml of dichloromethane each time. The dichloromethane phases are combined, dried over magnesium sulphate and concentrated to dryness by evaporation. The crude product is purified by chromatography on 150 g of silica gel (0.063-0.2 mm) using ethyl acetate as the eluant. The main eluate, which is concentrated by evaporation, is treated with ethereal hydrochloric acid to yield 1-[2-(chroman-3-yl)ethyl]-1,2,5,6-tetrahydropyridine-3-carboxylic acid methyl ester hydrochloride having a melting point of 175°-177°.

後処理

  1. stirringStirring
  2. stirringby shaking
  3. dry with materialdried over magnesium sulphate
  4. concentrationconcentrated to dryness by evaporation
  5. customThe crude product is purified by chromatography on 150 g of silica gel (0.063-0.2 mm)
  6. concentrationThe main eluate, which is concentrated by evaporation
  7. additionis treated with ethereal hydrochloric acid

出典と根拠

ORDレコード
ord-9d8900634d3545888adbdb8e5a9cf902
出典データセット
uspto-grants-1990_09
特許番号
US04957928

反応ノート

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