Ozone → tert-Butyl alpha-(2-Hydroxyethyl)-3-(2-methylpropyl)-2-oxo-1-(2-phenylethyl)-3-pyrrolidineacetate

HRID 727528Notes

Reaction equation

HRID 727528 reaction equation
[O:1]=[O+][O-].[CH3:4][CH:5]([CH3:32])[CH2:6][C:7]1([CH:21]([C:29](C)=[CH2:30])[C:22]([O:24][C:25]([CH3:28])([CH3:27])[CH3:26])=[O:23])[CH2:11][CH2:10][N:9]([CH2:12][CH2:13][C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[C:8]1=[O:20].[BH4-].[Na+]>CCO>[OH:1][CH2:30][CH2:29][CH:21]([C:7]1([CH2:6][CH:5]([CH3:4])[CH3:32])[CH2:11][CH2:10][N:9]([CH2:12][CH2:13][C:14]2[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=2)[C:8]1=[O:20])[C:22]([O:24][C:25]([CH3:28])([CH3:26])[CH3:27])=[O:23]

Participants

5

Reactant 3

HCID 24823OzoneHCID 4311764Sodium borohydrideHCID 19705553tert-Butyl 3-(2-Methylpropyl)-2-oxo-1-(2-phenylethyl)-alpha-(propen-2-yl)-3-pyrrolidineacetate

Product 1

HCID 19705471tert-Butyl alpha-(2-Hydroxyethyl)-3-(2-methylpropyl)-2-oxo-1-(2-phenylethyl)-3-pyrrolidineacetateYield 91%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Ozone is bubbled through a solution of tert-butyl 3-(2-methylpropyl)-2-oxo-1-(2-phenylethyl)-α-(propen-2-yl)-3-pyrrolidineacetate (555 mg, 1.39 mmol) and EtOH (12 mL) at -78° C. for 5 minutes. Nitrogen is then bubbled through the solution for 5 minutes. Sodium borohydride (79 mg, 2.1 mmol) is added and the mixture is allowed to warm slowly and to stir at room temperature overnight. The mixture is concentrated to near dryness, and aqueous workup (EtOAc, MgSO4) to give 511 mg (91%) of the title compound as a colorless oil.

Workup

  1. customNitrogen is then bubbled through the solution for 5 minutes
  2. temperatureto warm slowly
  3. concentrationThe mixture is concentrated

Sources & evidence

ORD record
ord-27b7e2b58d5c4a919eecd324addd7f03
Source dataset
uspto-grants-1998_01
Patent number
US05712300

Reaction notes

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