Aluminium lithium hydride → (2RS,5SR)-[5-(4-fluoro-phenyl)-1-(toluene-4-sulfonyl)-pyrrolidin-2-yl]-methanol

HRID 890254Notes

Reaction equation

HRID 890254 reaction equation
C[O:2][C:3]([CH:5]1[CH2:9][CH2:8][CH:7]([C:10]2[CH:15]=[CH:14][C:13]([F:16])=[CH:12][CH:11]=2)[N:6]1[S:17]([C:20]1[CH:25]=[CH:24][C:23]([CH3:26])=[CH:22][CH:21]=1)(=[O:19])=[O:18])=O.[H-].[Al+3].[Li+].[H-].[H-].[H-].C(OCC)C.CCCCCC>C1COCC1>[F:16][C:13]1[CH:12]=[CH:11][C:10]([CH:7]2[N:6]([S:17]([C:20]3[CH:21]=[CH:22][C:23]([CH3:26])=[CH:24][CH:25]=3)(=[O:19])=[O:18])[CH:5]([CH2:3][OH:2])[CH2:9][CH2:8]2)=[CH:15][CH:14]=1

Participants

5

Reactant 3

HCID 21226445Aluminium lithium hydrideHCID 21584099Diethylether hexaneHCID 69596768(2RS,5SR)-5-(4-Fluoro-phenyl)-1-(toluene-4-sulfonyl)-pyrrolidine-2-carboxylic acid methyl ester

Product 1

HCID 22250435(2RS,5SR)-[5-(4-fluoro-phenyl)-1-(toluene-4-sulfonyl)-pyrrolidin-2-yl]-methanol

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Reduction of (2RS,5SR)-5-(4-fluoro-phenyl)-1-(toluene-4-sulfonyl)-pyrrolidine-2-carboxylic acid methyl ester with lithium aluminum hydride (1.5 eq.) in THF at RT, aqueous work-up and crystallization from diethyl ether/hexane yielded the title compound, white solid, m.p. 82° C. and MS: m/e=350 (M+H+).

Sources & evidence

ORD record
ord-f7e96c3c45d249b0b1476d68085d0b26
Source dataset
uspto-grants-2006_02
Patent number
US06995182B2

Reaction notes

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