Sodium borohydride → HCID 86586760, compound

HRID 2088211Notes

Reaction equation

HRID 2088211 reaction equation
[BH4-].[Na+].[CH2:3]([N:10]1[C@@H:15]2[C@H:16]([C:18]3[N:19]=[N:20][N:21]([CH2:23][C:24](=[O:26])[CH3:25])[N:22]=3)[CH2:17][C@@:11]1([C:43]1[CH:48]=[CH:47][CH:46]=[CH:45][CH:44]=1)[C@H:12]([O:27][CH2:28][C:29]1[CH:34]=[C:33]([C:35]([F:38])([F:37])[F:36])[CH:32]=[C:31]([C:39]([F:42])([F:41])[F:40])[CH:30]=1)[CH2:13][CH2:14]2)[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1>CO.C1COCC1>[CH2:3]([N:10]1[C@@H:15]2[C@H:16]([C:18]3[N:19]=[N:20][N:21]([CH2:23][CH:24]([OH:26])[CH3:25])[N:22]=3)[CH2:17][C@@:11]1([C:43]1[CH:48]=[CH:47][CH:46]=[CH:45][CH:44]=1)[C@H:12]([O:27][CH2:28][C:29]1[CH:34]=[C:33]([C:35]([F:36])([F:37])[F:38])[CH:32]=[C:31]([C:39]([F:41])([F:42])[F:40])[CH:30]=1)[CH2:13][CH2:14]2)[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1

Participants

5

Reactant 2

HCID 4311764Sodium borohydrideHCID 86586761HCID 86586761, compound2×

Product 1

HCID 86586760HCID 86586760, compoundYield 95%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

Sodium borohydride (13 mg, 0.34 mmol) was added to a solution of (1R*,2R*,5S*,6R*)-8-benzyl-2-{[3,5-bis(trifluoromethyl)phenyl]methoxy}-6-[2-(2-oxopropyl)-2H-tetrazol-5-yl]-1-phenyl-8-azabicyclo[3.2.1]octane (Compound 3i in Table 3; 0.2 g, 0.31 mmol) in methanol (10 ml) and THF (2 ml). The mixture was stirred at room temperature for 18 hours. The reaction mixture was concentrated in vacuo and the residue partitioned between saturated sodium hydrogen carbonate and ethyl acetate. The organic layer was separated, dried (MgSO4), filtered and concentrated. The residue was chromatographed on silica gel eluting with 25 and 35% ethyl acetate/iso-hexanes to yield the title compound (189 mg, 95%).

Workup

  1. concentrationThe reaction mixture was concentrated in vacuo
  2. customthe residue partitioned between saturated sodium hydrogen carbonate and ethyl acetate
  3. customThe organic layer was separated
  4. dry with materialdried (MgSO4)
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe residue was chromatographed on silica gel eluting with 25 and 35% ethyl acetate/iso-hexanes

Sources & evidence

ORD record
ord-d7437bb7ec83427b82f7c2fef638ea28
Source dataset
uspto-grants-2004_04
Patent number
US06727249B2

Reaction notes

Loading…