Ozone → HCID 90048554, compound

HRID 884381Notes

Reaction equation

HRID 884381 reaction equation
[O:1]=[O+][O-].[CH2:4]([O:6][C:7]([C@@H:9]1[CH2:13][CH2:12][CH:11]([CH2:14][CH:15]=C)[N:10]1[C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18])=[O:8])[CH3:5].[BH4-].[Na+]>CO.C(Cl)Cl>[CH2:4]([O:6][C:7]([C@@H:9]1[CH2:13][CH2:12][CH:11]([CH2:14][CH2:15][OH:1])[N:10]1[C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18])=[O:8])[CH3:5]

Participants

6

Reactant 3

HCID 24823OzoneHCID 4311764Sodium borohydrideHCID 682243021-tert-Butyl 2-ethyl (2S)-5-(prop-2-en-1-yl)pyrrolidine-1,2-dicarboxylate

Product 1

HCID 90048554HCID 90048554, compoundYield 68%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6344DichloromethaneSolvent

Procedure

Ozone was passed at −78° C. through a solution of 1.00 g of 169 (3.53 mmol) in a mixture of 12 ml of MeOH and 6 ml of CH2Cl2 until the solution turned blue. The reaction was subsequently terminated and excess ozone removed by purging with oxygen. Thereafter, 270 mg of NaBH4 (7.06 mmol, 2 eq.) was added and the mixture stirred overnight to allow warming to RT. After checking completion of the reaction by means of TLC (EE/CH 1:1), the batch was concentrated and the remaining residue taken up in 60 ml of CH2Cl2 and 40 ml of half-conc. NaCl solution. The aqueous phase was extracted with 3×20 ml of CH2Cl2, the combined organic phases were dried over MgSO4 and concentrated. The residue was purified using silica gel column chromatography (EEICH 1:1) to obtain 691 mg (2.40 mmol, 68%) of alcohol 170 as a mixture of epimers (colorless oil).

Workup

  1. customThe reaction was subsequently terminated
  2. customexcess ozone removed
  3. customby purging with oxygen
  4. customcompletion of the reaction by means of TLC (EE/CH 1:1)
  5. concentrationthe batch was concentrated
  6. extractionThe aqueous phase was extracted with 3×20 ml of CH2Cl2
  7. dry with materialthe combined organic phases were dried over MgSO4
  8. concentrationconcentrated
  9. customThe residue was purified

Sources & evidence

ORD record
ord-ad1fd7b90b9b41d686b8bf929eb3cd68
Source dataset
uspto-grants-2012_08
Patent number
US08242105B2

Reaction notes

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