Sodium borohydride → HCID 10302951, compound

HRID 896678Notes

Reaction equation

HRID 896678 reaction equation
C([O:3][C:4](=O)[C:5]([F:40])([C:30]1[CH:35]=[CH:34][C:33]([S:36]([CH3:39])(=[O:38])=[O:37])=[CH:32][CH:31]=1)[CH2:6][C:7]1[CH:12]=[CH:11][CH:10]=[C:9]([C:13]2[CH:14]=[C:15]([C:23]([S:26]([CH3:29])(=[O:28])=[O:27])([CH3:25])[CH3:24])[CH:16]=[C:17]3[C:22]=2[N:21]=[CH:20][CH:19]=[CH:18]3)[CH:8]=1)C.CC(C[Al]CC(C)C)C.[BH4-].[Na+]>C(Cl)Cl.[Cl-].[NH4+].C(OCC)(=O)C>[F:40][C:5]([C:30]1[CH:35]=[CH:34][C:33]([S:36]([CH3:39])(=[O:38])=[O:37])=[CH:32][CH:31]=1)([CH2:6][C:7]1[CH:12]=[CH:11][CH:10]=[C:9]([C:13]2[CH:14]=[C:15]([C:23]([S:26]([CH3:29])(=[O:27])=[O:28])([CH3:24])[CH3:25])[CH:16]=[C:17]3[C:22]=2[N:21]=[CH:20][CH:19]=[CH:18]3)[CH:8]=1)[CH2:4][OH:3]

Participants

7

Reactant 3

HCID 4311764Sodium borohydrideHCID 10145327HCID 10145327, compoundHCID 16682954Dibah

Product 1

HCID 10302951HCID 10302951, compound

Reagents, catalysts & solvents 3

HCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolventHCID 25517Ammonium ChlorideSolvent

Conditions

Temperature
-78 °C

Procedure

To a solution of Example 27 (1.15 g, 1.95 mmol) in CH2Cl2 (80 mL) at −78° C. was added dibal-H (0.82 mL, 4.6 mmol). The resulting reaction mixture was stirred 1 h at −78° C., then quenched with sodium potassium tartrate solution and stirred at 21° C. for 3 h. The organic extracts were washed (H2O), (brine), dried (MgSO4), filtered and concentrated. To the residue dissolved in THF/MeOH (2:1, 22 mL) at 21° C. was added NaBH4 (180 mg, 4.9 mmol). After 12 h, the reaction mixture was diluted with a saturated ammonium chloride solution and ethyl acetate. The organic extracts were washed (H2O), (brine), dried (MgSO4), filtered and concentrated to provided the title compound as a white solid.

Workup

  1. customThe resulting reaction mixture
  2. customquenched with sodium potassium tartrate solution
  3. stirringstirred at 21° C. for 3 h
  4. washThe organic extracts were washed (H2O), (brine),
  5. dry with materialdried (MgSO4)
  6. filtrationfiltered
  7. concentrationconcentrated
  8. dissolutionTo the residue dissolved in THF/MeOH (2:1, 22 mL) at 21° C.
  9. waitAfter 12 h
  10. washThe organic extracts were washed (H2O), (brine),
  11. dry with materialdried (MgSO4)
  12. filtrationfiltered
  13. concentrationconcentrated

Sources & evidence

ORD record
ord-183dce116bd146efa31f81bf7d6181af
Source dataset
uspto-grants-2005_07
Patent number
US06919353B2

Reaction notes

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