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Hydrochloric Acid → benzyl (2R, 4S)-2-(4,5-diphenyloxazol-2-yl)-4-hydroxypyrrolidine-1-carboxylate

HRID 431759
Notes
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Reaction equation

HRID 431759 reaction equation
C([O:4][C@@H:5]1[CH2:9][N:8]([C:10]([O:12][CH2:13][C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)=[O:11])[C@@H:7]([C:20]2[O:21][C:22]([C:31]3[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=3)=[C:23]([C:25]3[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=3)[N:24]=2)[CH2:6]1)(=O)C.C[O-].[Na+].Cl>CC#N.CO>[C:25]1([C:23]2[N:24]=[C:20]([C@H:7]3[CH2:6][C@H:5]([OH:4])[CH2:9][N:8]3[C:10]([O:12][CH2:13][C:14]3[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=3)=[O:11])[O:21][C:22]=2[C:31]2[CH:32]=[CH:33][CH:34]=[CH:35][CH:36]=2)[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 10942334Sodium MethoxideHCID 86759291benzyl (2R, 4S)-4-acetoxy-2-(4,5-diphenyloxazol-2-yl)pyrrolidine-1-carboxylate

Product 1

HCID 86759292benzyl (2R, 4S)-2-(4,5-diphenyloxazol-2-yl)-4-hydroxypyrrolidine-1-carboxylateYield 72.1%

Reagents, catalysts & solvents 2

HCID 887
Methanol
Solvent
HCID 6342AcetonitrileSolvent

Procedure

To a solution of benzyl (2R, 4S)-4-acetoxy-2-(4,5-diphenyloxazol-2-yl)pyrrolidine-1-carboxylate (1.49 g) in MeCN (15 mL) was added 28% sodium methylate in MeOH (0.72 mL) at 5° C., and the mixture was stirred at the same temperature for 30 minutes. To the reaction mixture was added 1N HCl (3.8 mL) under ice-cooling, and extracted with EtOAc. The organic layer was washed with water, saturated sodium hydrogen carbonate solution, water and brine, dried (MgSO4), and evaporated in vacuo. The residue was purified by silica gal column chromatography (hexane-EtOAc, 1:3 elution) to give benzyl (2R, 4S)-2-(4,5-diphenyloxazol-2-yl)-4-hydroxypyrrolidine-1-carboxylate (980.8 mg).

Workup

  1. temperaturecooling
  2. extractionextracted with EtOAc
  3. washThe organic layer was washed with water, saturated sodium hydrogen carbonate solution, water and brine
  4. dry with materialdried (MgSO4)
  5. customevaporated in vacuo
  6. customThe residue was purified by silica gal column chromatography (hexane-EtOAc, 1:3 elution)

Sources & evidence

ORD record
ord-79e388c0650c44bd9f20e9d184395fb3
Source dataset
uspto-grants-2003_12
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US06660759B1

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes