Sodium hydride → 1-Benzylpyrrolidine-3-carbaldehyde

HRID 1762916

反応式

HRID 1762916 の反応式
[C:1]1([CH2:7][N:8]2[CH2:12][CH2:11][CH:10]([CH2:13][OH:14])[CH2:9]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[Cr](Cl)([O-])(=O)=O.[NH+]1[CH:25]=[CH:24]C=CC=1.CS(C)(=O)=C.[I-].C[S+](C)(C)=[O:34].[H-].[Na+].[O-:39][C:40]1[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=1.[Na+]>>[C:1]1([CH2:7][N:8]2[CH2:12][CH2:11][CH:10]([CH:13]=[O:14])[CH2:9]2)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1.[C:1]1([CH2:7][N:8]2[CH2:9][CH2:10][CH2:11][CH:12]2[CH:24]([CH2:25][O:39][C:40]2[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=2)[OH:34])[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

参加物

8

反応物 6

HCID 24758Sodium hydrideHCID 74498Sulfoxonium, trimethyl-, iodide (1:1)HCID 4445035Phenolate SodiumHCID 5176654(1-Benzylpyrrolidin-3-yl)methanolHCID 6396768Dimethylsulfoxonium methylideHCID 178418287HCID 178418287、化合物

生成物 2

HCID 45894781-Benzylpyrrolidine-3-carbaldehydeHCID 200397871-Phenylmethyl-alpha-phenoxymethyl-2-pyrrolidinemethanol

実験手順

1-Phenylmethyl-3-formylpyrrolidine is prepared from 1-phenylmethyl-3-hydroxymethyl pyrrolidine (source: method of U.S. Pat. No. 3,318,908) by reacting it with pyridinium chlorochromate and converted to the corresponding 3-epoxide using dimethyloxosulfonium methylide obtained by mixing trimethylsulfoxonium iodide and sodium hydride in aprotic solvent. The epoxide is reacted with sodium phenoxide and the reaction mixture is acidified to give 1-phenylmethyl-α-phenoxymethyl-2-pyrrolidinemethanol which is hydrogenated over palladium on carbon to give the free base of the title compound. The free base is converted to the hydrochloride salt as in Example 38.

後処理

  1. customobtained

出典と根拠

ORDレコード
ord-00ddace851d442d699fafbac4cf28083
出典データセット
uspto-grants-1989_05
特許番号
US04835164

関連ノート

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