Water → HCID 22591688, compound

HRID 22841Notes

Reaction equation

HRID 22841 reaction equation
[F:1][C:2]([F:29])([F:28])[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[C:9]1[O:13][C:12]([C:14]23[CH2:21][CH2:20][C:17]([CH2:22][CH2:23][CH2:24][C:25](=[O:27])[CH3:26])([CH2:18][CH2:19]2)[CH2:16][CH2:15]3)=[N:11][N:10]=1.[BH4-].[Na+].C(OCC)(=O)C.O>CO>[F:29][C:2]([F:1])([F:28])[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[C:9]1[O:13][C:12]([C:14]23[CH2:19][CH2:18][C:17]([CH2:22][CH2:23][CH2:24][CH:25]([OH:27])[CH3:26])([CH2:16][CH2:15]2)[CH2:20][CH2:21]3)=[N:11][N:10]=1

Participants

6

Reactant 4

HCID 962WaterHCID 8857Ethyl AcetateHCID 4311764Sodium borohydrideHCID 22591701HCID 22591701, compound

Product 1

HCID 22591688HCID 22591688, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

5-(4-{5-[2-(Trifluoromethyl)phenyl]-1,3,4-oxadiazol-2-yl}bicyclo[2.2.2]oct-1-yl)pentan-2-one (4-H) (0.072 g) was stirred in methanol (2 mL) at 0° C. Sodium borohydride (20 mg) was added. The reaction was allowed to stir to room temperature. The mixture was then layered with ethyl acetate (15 mL) and water (15 mL). The ethyl acetate layer was extracted and dried (MgSO4). Solvent was removed in vacuo to afford pure 5-(4-{5-[2-(trifluoromethyl)phenyl]-1,3,4-oxadiazol-2-yl}bicyclo[2.2.2]oct-1-yl)pentan-2-ol (4-I).

Workup

  1. extractionThe ethyl acetate layer was extracted
  2. dry with materialdried (MgSO4)
  3. customSolvent was removed in vacuo

Sources & evidence

ORD record
ord-777d428697504cfeb9ba3a5dddb43036
Source dataset
uspto-grants-2005_02
Patent number
US06849636B2

Reaction notes

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