Sodium borohydride → HCID 71522897, compound

HRID 1621016Notes

Reaction equation

HRID 1621016 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[C:7]([C:9]1([CH:13]2[CH2:17][CH2:16][N:15]([C:18]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19])[CH2:14]2)[CH2:12][CH2:11][CH2:10]1)=[O:8].[BH4-].[Na+]>C1COCC1.CO>[OH:8][CH:7]([C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][N:1]=1)[C:9]1([CH:13]2[CH2:17][CH2:16][N:15]([C:18]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19])[CH2:14]2)[CH2:12][CH2:11][CH2:10]1

Participants

5

Reactant 2

HCID 4311764Sodium borohydrideHCID 89524760HCID 89524760, compound

Product 1

HCID 71522897HCID 71522897, compoundYield 77%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of Example 265D (140 mg, 0.43 mmol) in THF (4 mL) and MeOH (4 mL) was added NaBH4 (60 mg, 2.5 mmol) and the solution was stirred at room temperature for 2 hours. The reaction mixture was quenched with saturated NH4Cl solution and the resulting mixture extracted with EtOAc (10 mL×3). The combined organic phases were washed with brine (10 mL), dried over Na2SO4, filtered, and concentrated. The residue was purified by Prep-HPLC to obtain the title compound (0.11 g, 76% yield) as a white solid. MS: m/z 333 (M+H); 1H NMR: (400 MHz, CDCl3): δ 8.57 (d, J=4.3 Hz, 1H), 7.67 (t, J=6.8 Hz, 1H), 7.31-7.23 (m, 2H), 4.73 (s, 1H), 4.55-4.43 (m, 1H), 3.56-3.26 (m, 2H), 3.13-2.79 (m, 2H), 2.28-2.07 (m, 3H), 2.05-1.85 (m, 2H), 1.75-1.70 (m, 4H), 1.46 (s, 9H).

Workup

  1. customThe reaction mixture was quenched with saturated NH4Cl solution
  2. extractionthe resulting mixture extracted with EtOAc (10 mL×3)
  3. washThe combined organic phases were washed with brine (10 mL)
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe residue was purified by Prep-HPLC

Sources & evidence

ORD record
ord-a8d8330944304af0a7f1185ec7171b22
Source dataset
uspto-grants-2014_07
Patent number
US08772500B2

Reaction notes

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