Sodium borohydride → HCID 11545495, compound

HRID 2214960Notes

Reaction equation

[CH3:1][N:2]([CH2:4][CH:5]1[C:9](=[O:10])[C:8]([C:11]2[CH:12]=[C:13]([CH3:17])[CH:14]=[CH:15][CH:16]=2)=[C:7]([C:18]2[CH:23]=[CH:22][C:21]([S:24]([CH3:27])(=[O:26])=[O:25])=[CH:20][CH:19]=2)[CH2:6]1)[CH3:3].[BH4-].[Na+]>>[CH3:1][N:2]([CH2:4][CH:5]1[CH:9]([OH:10])[C:8]([C:11]2[CH:12]=[C:13]([CH3:17])[CH:14]=[CH:15][CH:16]=2)=[C:7]([C:18]2[CH:19]=[CH:20][C:21]([S:24]([CH3:27])(=[O:26])=[O:25])=[CH:22][CH:23]=2)[CH2:6]1)[CH3:3]

Participants

Reactant 2

HCID 4311764Sodium borohydride

HCID 11523826HCID 11523826, compound

Product 1

HCID 11545495HCID 11545495, compound

Procedure

2.28 g of 5-dimethylaminomethyl-3-(4-methanesulfonylphenyl)-2m-tolyl-cyclopent-2-enone were reacted in a manner similar to the method described in Example 21 with 0.62 g of sodium borohydride to yield 5-dimethylaminomethyl-3-(4-methanesulfonylphenyl)-2m-tolyl-cyclopent-2-enol. After purification by column chromatography and precipitation of the hydrochloride with a hydrogen chloride/diethyl ether mixture, 0.95 g (corresponding to 41.4% of theoretical) were obtained in the form of colourless crystals with a melting point of 165–167° C.

Sources & evidence

ORD record: ord-ba9b595155144b7da6018ebbec2ac173
Source dataset: uspto-grants-2006_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07109214B2

Reaction notes

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