Nitrogen → HCID 19705520, compound

HRID 727546Notes

Reaction equation

HRID 727546 reaction equation
[O:1]=[O+][O-].[CH3:4][CH:5]([CH3:31])[CH2:6][C:7]1([CH:20]([C:28](C)=[CH2:29])[C:21]([O:23][C:24]([CH3:27])([CH3:26])[CH3:25])=[O:22])[CH2:11][CH2:10][N:9]([CH2:12][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[C:8]1=[O:19].N#N.[BH4-].[Na+]>CCO>[OH:1][CH2:29][CH2:28][CH:20]([C:7]1([CH2:6][CH:5]([CH3:31])[CH3:4])[CH2:11][CH2:10][N:9]([CH2:12][C:13]2[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=2)[C:8]1=[O:19])[C:21]([O:23][C:24]([CH3:27])([CH3:26])[CH3:25])=[O:22]

Participants

6

Reactant 4

HCID 947NitrogenHCID 24823OzoneHCID 4311764Sodium borohydrideHCID 19705562HCID 19705562, compound

Product 1

HCID 19705520HCID 19705520, compoundYield 64%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Ozone is bubbled through a cold (-78° C.) solution of tert-butyl 3-(2-methylpropyl)-2-oxo-1-(phenylmethyl)-α-(propen-2-yl)-3-pyrrolidineacetate (1.32 g, 3.42 mmol) in EtOH (30 mL). After purging the solution with N2, sodium borohydride (195 mg, 5.14 mmol) is added in one portion (at -78° C.). The solution is allowed to slowly warm to room temperatuare under N2 overnight. The reaction mixture is concentrated to a white solid, diluted with H2O (10 mL) and extracted with EtOAc (3×25 mL). The organic extracts are combined, washed with brine (25 mL), dried over anhydrous Na2SO4, filtered, and concentrated under reduced pressure to yield 1.37 g of a clear, colorless oil. The oil is purified by silica gel chromatography (50 g SG, 20% EtOAc/hexane) to give 850 mg (64%) of the title compound as a clear, colorless oil, which is a single diastereomer.

Workup

  1. additionis added in one portion (at -78° C.)
  2. temperatureto slowly warm to room temperatuare under N2 overnight
  3. concentrationThe reaction mixture is concentrated to a white solid
  4. additiondiluted with H2O (10 mL)
  5. extractionextracted with EtOAc (3×25 mL)
  6. washwashed with brine (25 mL)
  7. dry with materialdried over anhydrous Na2SO4
  8. filtrationfiltered
  9. concentrationconcentrated under reduced pressure
  10. customto yield 1.37 g of a clear, colorless oil
  11. customThe oil is purified by silica gel chromatography (50 g SG, 20% EtOAc/hexane)

Sources & evidence

ORD record
ord-6dff4e9c8664499ba8e1100e7e5a3a9f
Source dataset
uspto-grants-1998_01
Patent number
US05712300

Reaction notes

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