Acetone → HCID 11599037, compound

HRID 1993989Notes

Reaction equation

HRID 1993989 reaction equation
[F:1][C:2]([F:34])([F:33])[C:3]1[CH:4]=[C:5]([C@H:13]([O:15][C@H:16]2[O:24][CH2:23][C@@H:19]3[CH2:20][NH:21][CH2:22][C@H:18]3[C@@H:17]2[C:25]2[CH:30]=[CH:29][C:28]([F:31])=[CH:27][C:26]=2[CH3:32])[CH3:14])[CH:6]=[C:7]([C:9]([F:12])([F:11])[F:10])[CH:8]=1.[CH3:35][C:36]([CH3:38])=O.[BH-](OC(C)=O)(OC(C)=O)OC(C)=O.[Na+]>C(Cl)Cl.CC(O)=O>[F:34][C:2]([F:1])([F:33])[C:3]1[CH:4]=[C:5]([C@H:13]([O:15][C@H:16]2[O:24][CH2:23][C@@H:19]3[CH2:20][N:21]([CH:36]([CH3:38])[CH3:35])[CH2:22][C@H:18]3[C@@H:17]2[C:25]2[CH:30]=[CH:29][C:28]([F:31])=[CH:27][C:26]=2[CH3:32])[CH3:14])[CH:6]=[C:7]([C:9]([F:12])([F:10])[F:11])[CH:8]=1

Participants

6

Reactant 3

HCID 180AcetoneHCID 5049666Sodium triacetoxyborohydrideHCID 11648859HCID 11648859, compound

Product 1

HCID 11599037HCID 11599037, compound

Reagents, catalysts & solvents 2

HCID 176Acetic AcidCatalystHCID 6344DichloromethaneSolvent2×

Procedure

To a solution of (3aS,6R,7R,7aR)-6-{(1R)-1-[3,5-bis(trifluoromethyl)phenyl]ethoxy}-7-(4-fluoro-2-methylphenyl)octahydropyrano[3,4-c]pyrrole (29.6 mg, 0.06 mmol), acetone (0.044 mL, 0.60 mmol) and NaB(OAc)3H (69 mg, 0.33 mmol) in DCM was added 1 drop of HOAc and was stirred at rt for 16 hr. The mixture was diluted with DCM and was washed with NaHCO3. The organic phase was dried with Na2SO4, filtered and concentrated. The crude was purified by reverse phase HPLC to afford the title compound. MS: (MH)+534.

Workup

  1. washwas washed with NaHCO3
  2. dry with materialThe organic phase was dried with Na2SO4
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customThe crude was purified by reverse phase HPLC

Sources & evidence

ORD record
ord-09e160336e044d1cb32d8d24e5d00a42
Source dataset
uspto-grants-2010_01
Patent number
US07652058B2

Reaction notes

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