Sodium hydride → 1-Benzylpyrrolidine-3-carbaldehyde

HRID 1762916

반응식

HRID 1762916 반응식
[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

참가 물질

8

반응물 6

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

생성물 2

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

실험 절차

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.

후처리

  1. customobtained

출처 및 근거

ORD 기록
ord-00ddace851d442d699fafbac4cf28083
출처 데이터셋
uspto-grants-1989_05
특허 번호
US04835164

연결된 노트

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