Pyridine → HCID 86584850, compound

HRID 1006813Notes

Reaction equation

HRID 1006813 reaction equation
[SH:1][C@H:2]1[CH2:6][N:5]([S:7]([CH3:10])(=[O:9])=[O:8])[C@H:4]([CH2:11][OH:12])[CH2:3]1.N1C=CC=CC=1.[C:19](OC(=O)C)(=[O:21])[CH3:20]>ClCCl>[OH:12][CH2:11][C@H:4]1[N:5]([S:7]([CH3:10])(=[O:9])=[O:8])[CH2:6][C@H:2]([S:1][C:19](=[O:21])[CH3:20])[CH2:3]1

Participants

5

Reactant 3

HCID 1049PyridineHCID 7918Acetic AnhydrideHCID 86584851HCID 86584851, compound

Product 1

HCID 86584850HCID 86584850, compoundYield 23.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of (2S,4R)-(4-mercapto-1-methanesulfonyl-pyrrolidin-2-yl)-methanol (0.28 g) in dichloromethane (10 ml) were added pyridine (0.131 g) and acetic anhydride (0.160 g). The reaction mixture was stirred for 4 h at room temperature, treated with ice/water and extracted with EtOAc. The organic phase was washed with a saturated solution of sodium bicarbonate and brine, dried over magnesium sulphate and concentrated. The residue was chromatographed on silica gel using EtOAc/hexane 1:2 as eluent to obtain thioacetic acid (3R,5S)-S-(5-hydroxymethyl-1-methanesulfonyl-pyrrolidin-3-yl) ester (0.080 g) as a viscous oil.

Workup

  1. extractionextracted with EtOAc
  2. washThe organic phase was washed with a saturated solution of sodium bicarbonate and brine
  3. dry with materialdried over magnesium sulphate
  4. concentrationconcentrated
  5. customThe residue was chromatographed on silica gel

Sources & evidence

ORD record
ord-1ef822e4a9e9483a8cb119c7fcf4a99e
Source dataset
uspto-grants-2004_09
Patent number
US06790860B2

Reaction notes

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