Sodium hydride → 1-Benzylpyrrolidine-3-carbaldehyde

HRID 1762916

Reaction equation

HRID 1762916 reaction equation
[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

Participants

8

Reactant 6

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

Product 2

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

Procedure

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.

Workup

  1. customobtained

Sources & evidence

ORD record
ord-00ddace851d442d699fafbac4cf28083
Source dataset
uspto-grants-1989_05
Patent number
US04835164

Linked notes

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