Sodium borohydride → HCID 71523446, compound

HRID 1621009Notes

Reaction equation

HRID 1621009 reaction equation
[OH:1][C:2]1([C:7]2([C:11]([C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][N:14]=3)=[O:12])[CH2:10][CH2:9][CH2:8]2)[CH2:6][CH2:5][O:4][CH2:3]1.[BH4-].[Na+]>CO>[OH:12][CH:11]([C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][N:14]=1)[C:7]1([C:2]2([OH:1])[CH2:6][CH2:5][O:4][CH2:3]2)[CH2:10][CH2:9][CH2:8]1

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 89524916HCID 89524916, compound

Product 1

HCID 71523446HCID 71523446, compoundYield 33.4%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of Example 246B (15 mg, 0.06 mmol) in MeOH (5 mL) was added NaBH4 (13 mg, 0.34 mmol) in one portion. The mixture was stirred at room temperature for 2 hours. The reaction mixture was quenched with aqueous NH4Cl solution and extracted with EtOAc (20 mL×2). The combined organic phase was washed with brine (10 mL), dried over Na2SO4, filtered, and concentrated. The residue was purified by Prep-HPLC to obtain the title compounds as corloless oils (5.0 mg, yield 30%). MS (M+1) δ 250.2; 1H NMR: (400 MHz, CDCl3): δ 8.60 (d, J=3.6 Hz, 1H), 7.76-7.72 (m, 1H), 7.49-7.46 (m, 1H), 7.31-7.28 (m, 1H), 4.96 (s, 1H), 4.84 (brs, 1H), 4.09-3.83 (m, 3H), 3.76 (d, J=9.6 Hz, 0.66H), 3.56 (d, J=10.0 Hz, 0.44H), 2.27-2.14 (m, 1H), 2.08-1.80 (m, 5H), 1.68-1.50 (m, 1H), 1.16-1.04 (m, 0.67H), 0.95-0.83 (m, 0.48H).

Workup

  1. customThe reaction mixture was quenched with aqueous NH4Cl solution
  2. extractionextracted with EtOAc (20 mL×2)
  3. washThe combined organic phase was 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-f5ec51589fce432e9b0fbeaa2fe7f95c
Source dataset
uspto-grants-2014_07
Patent number
US08772500B2

Reaction notes

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