Chlorzoxazone → (3S)-N-(5-chloro-2-hydroxyphenyl)-3-hydroxypyrrolidine-1-carboxamide

HRID 270113Notes

Reaction equation

HRID 270113 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[O:9][C:8](=[O:10])[NH:7][C:6]=2[CH:11]=1.[NH:12]1[CH2:16][CH2:15][C@H:14]([OH:17])[CH2:13]1>>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([OH:9])=[C:6]([NH:7][C:8]([N:12]2[CH2:16][CH2:15][C@H:14]([OH:17])[CH2:13]2)=[O:10])[CH:11]=1

Participants

3

Reactant 2

HCID 2733ChlorzoxazoneHCID 2733874(3S)-pyrrolidin-3-ol

Product 1

HCID 68963403(3S)-N-(5-chloro-2-hydroxyphenyl)-3-hydroxypyrrolidine-1-carboxamideYield 880%

Procedure

5-chloro-1,3-benzoxazole-2(3H)-one (577 mg, 0.34 mmol) and (3S)-pyrrolidin-3-ol (0.6 mL, 0.74 mmol) was heated to 90° C. for 2 hrs. The resulting red solidified oil was purified on silica (dichloromethane/methanol) to give the titled compound (768 mg, 88%).

Workup

  1. customwas purified on silica (dichloromethane/methanol)

Sources & evidence

ORD record
ord-3c3f915fa0da416aa7c54c03394e10c0
Source dataset
uspto-grants-2008_11
Patent number
US07449475B2

Reaction notes

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