Ozone → HCID 68688454, compound

HRID 1296264Notes

Reaction equation

HRID 1296264 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:28][CH2:27][N:11]2[C:12](=[O:26])[C:13]3[C:18]([C@@H:10]2[CH2:9]1)=[CH:17][C:16](/[CH:19]=C\C)=[CH:15][C:14]=3[C:22]([F:25])([F:24])[F:23])=[O:7])([CH3:4])([CH3:3])[CH3:2].[O:29]=[O+][O-].[BH4-].[Na+].C([O-])(O)=O.[Na+].C(OC(OC(C)(C)C)=O)(OC(C)(C)C)=O>CO.Cl.CCOC(C)=O>[C:1]([O:5][C:6]([N:8]1[CH2:28][CH2:27][N:11]2[C:12](=[O:26])[C:13]3[C:18]([C@@H:10]2[CH2:9]1)=[CH:17][C:16]([CH2:19][OH:29])=[CH:15][C:14]=3[C:22]([F:24])([F:23])[F:25])=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

9

Reactant 5

HCID 24823OzoneHCID 90495Di-tert-butyl dicarbonateHCID 516892Sodium BicarbonateHCID 4311764Sodium borohydrideHCID 68689588HCID 68689588, compound

Product 1

HCID 68688454HCID 68688454, compound

Reagents, catalysts & solvents 3

HCID 313Hydrochloric AcidSolventHCID 887MethanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a stirring solution of N-(t-butoxycarbonyl)-(R)-1,3,4,10b-tetrahydro-9-(cis-1-propenyl)-7-trifluoromethyl-pyrazino[2,1-a]isoindol-6(2H)-one (182 mg, 0.46 mmol) in MeOH (5.0 mL) at −78° C. was bubbled ozone for 5 min. until the reaction turned a light blue color. After 5 min., sodium borohydride (23 mg, 0.6 mmol) was added. The reaction was stir for 1 hr and then warmed to room temp. The reaction was conc. in vacuo to a white solid and then dissolved in 1M aq. HCl. After 15 min, the reaction was diluted with EtOAc, basefied with NaHCO3, and treated with di-t-butyl dicarbonate (125 mg, 0.58 mmol). After 1 h, the reaction was extracted with EtOAc (3×5 mL). The organic layers were combined, dried over Na2SO4, and conc. in vacuo to a colorless oil. The oil was purified by flash chromatography (silica gel, 0–50% EtOAc in hexanes) to give 141 mg of the desired product as a white solid. MS (ESI) 387 (M+H).

Workup

  1. waitAfter 15 min
  2. waitAfter 1 h
  3. extractionthe reaction was extracted with EtOAc (3×5 mL)
  4. dry with materialdried over Na2SO4
  5. customThe oil was purified by flash chromatography (silica gel, 0–50% EtOAc in hexanes)

Sources & evidence

ORD record
ord-d92708aa0d004303bdffae7a95aa6f5f
Source dataset
uspto-grants-2007_07
Patent number
US07244843B2

Reaction notes

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