Sodium cyanoborohydride → HCID 86709171, compound

HRID 1851117Notes

Reaction equation

HRID 1851117 reaction equation
[OH:1][C:2]([CH3:21])([CH3:20])[C@H:3]([N:5]1[C:13]2[C:8](=[C:9]([C:16]([F:19])([F:18])[F:17])[C:10]([C:14]#[N:15])=[CH:11][CH:12]=2)[CH:7]=[CH:6]1)[CH3:4].[BH3-]C#N.[Na+]>C(O)(C(F)(F)F)=O>[OH:1][C:2]([CH3:20])([CH3:21])[C@H:3]([N:5]1[C:13]2[C:8](=[C:9]([C:16]([F:19])([F:17])[F:18])[C:10]([C:14]#[N:15])=[CH:11][CH:12]=2)[CH2:7][CH2:6]1)[CH3:4]

Participants

4

Reactant 2

HCID 5003444Sodium cyanoborohydrideHCID 86709172HCID 86709172, compound

Product 1

HCID 86709171HCID 86709171, compound

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

To a solution of (R)-1-(3-hydroxy-3-methylbutan-2-yl)-4-(trifluoromethyl)-1H-indole-5-carbonitrile (Example 22) (0.017 g, 0.057 mmol) in TFA (1.5 mL), in an ice bath, was added NaCNBH3 (0.0721 g, 1.148 mmol) in portions. After stirring in the cold bath for 1 h, the reaction mixture was partially concentrated. The residue was dissolved in CH2Cl2 (20 mL) and washed with 0.5 N NaOH (10 mL). The organic phase was washed with 0.5 N NaOH (1×10 mL) and brine, dried over Na2SO4, filtered and concentrated. The residue was chromatographed over silica gel using a 10-40% EtOAc-hexane gradient to give (R)-1-(3-hydroxy-3-methylbutan-2-yl)-4-(trifluoromethyl)indoline-5-carbonitrile: MS (ESI): m/z 299 (M+H).

Workup

  1. concentrationthe reaction mixture was partially concentrated
  2. dissolutionThe residue was dissolved in CH2Cl2 (20 mL)
  3. washwashed with 0.5 N NaOH (10 mL)
  4. washThe organic phase was washed with 0.5 N NaOH (1×10 mL) and brine
  5. dry with materialdried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customThe residue was chromatographed over silica gel using a 10-40% EtOAc-hexane gradient

Sources & evidence

ORD record
ord-4effef0bd19e4e2a8a14c73ca16e72ef
Source dataset
uspto-grants-2015_02
Patent number
US08957104B2

Reaction notes

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