4-Toluenesulfonyl chloride → HCID 70130867, compound

HRID 1594768Notes

Reaction equation

HRID 1594768 reaction equation
C[O:2][C:3]([CH:5]1[CH2:9][CH2:8][N:7]([S:10]([C:13]2[CH:18]=[CH:17][C:16]([CH3:19])=[CH:15][CH:14]=2)(=[O:12])=[O:11])[CH:6]1[C:20]1[CH:25]=[CH:24][C:23]([F:26])=[CH:22][CH:21]=1)=O.COC(C1CCNC1C1C=CC(F)=CC=1)=O.C1(C)C=CC(S(Cl)(=O)=O)=CC=1.B.[Na]>CO>[F:26][C:23]1[CH:22]=[CH:21][C:20]([CH:6]2[CH:5]([CH2:3][OH:2])[CH2:9][CH2:8][N:7]2[S:10]([C:13]2[CH:14]=[CH:15][C:16]([CH3:19])=[CH:17][CH:18]=2)(=[O:12])=[O:11])=[CH:25][CH:24]=1

Participants

6

Reactant 4

HCID 73974-Toluenesulfonyl chlorideHCID 70075598HCID 70075598, compoundHCID 70078183HCID 70078183, compoundHCID 178418435HCID 178418435, compound

Product 1

HCID 70130867HCID 70130867, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Reduction of (2RS,3RS)-2-(4-fluoro-phenyl)-1-(toluene-4-sulfonyl)-pyrrolidine-3-carboxylic acid methyl ester, prepared from (2RS,3RS)-2-(4-fluoro-phenyl)-pyrrolidine-3-carboxylic acid methyl ester and toluene-4-sulfonyl chloride in accordance with the general method of example 1e, with sodium boron hydride in MeOH yielded after aqueous work-up and purification by column chromatography on silica gel (ethyl acetate/hexane 1:1) the title compound as a pale yellow oil, MS: m/e=348 (M−H+).

Workup

  1. customyielded
  2. customafter aqueous work-up and purification by column chromatography on silica gel (ethyl acetate/hexane 1:1) the title compound as a pale yellow oil, MS

Sources & evidence

ORD record
ord-b2c1b64b240e492198d15bf62b012255
Source dataset
uspto-grants-2001_09
Patent number
US06284785B1

Reaction notes

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