Sodium borohydride → HCID 178521393, compound

HRID 1023878Notes

Reaction equation

HRID 1023878 reaction equation
[NH:1]1[CH:5]=[C:4]([C:6]2[CH:21]=[CH:20][CH:19]=[CH:18][C:7]=2[O:8][CH2:9][C:10]([CH:12]2[CH2:17][CH2:16][CH2:15][CH2:14][CH2:13]2)=[O:11])[N:3]=[CH:2]1.[BH4-].[Na+]>CO>[NH:1]1[CH:5]=[C:4]([C:6]2[CH:21]=[CH:20][CH:19]=[CH:18][C:7]=2[O:8][CH2:9][CH:10]([CH:12]2[CH2:17][CH2:16][CH2:15][CH2:14][CH2:13]2)[OH:11])[N:3]=[CH:2]1

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 178521392HCID 178521392, compound

Product 1

HCID 178521393HCID 178521393, compoundYield 90.4%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a mixture 2-(2-(1H-imidazol-4-yl)phenoxy)-1-cyclohexylethanone (130 mg, 0.457 mmol) in MeOH (4 mL) at 0° C., was added NaBH4 (52 mg, 1.37 mmol) and the solution was allowed to stir at room temperature for 1 h. The solvent was distilled off and the crude was acidified with dil HCl (2 N) and again basified by saturated aqueous NaHCO3 solution, the product was extracted with EtOAc (3×15 mL). The combined organic extracts were washed with brine, dried, and concentrated under reduced pressure to afford the final product (118 mg, 0.413 mmol, 90%). 1H NMR (DMSO-d6): 1.04-1.21 (m, 5H), 1.49-1.50 (m, 1H), 1.61-1.68 (m, 4H), 1.85 (d, 1H, J=12.4 Hz), 3.62-3.65 (m, 1H), 3.96 (d, 1H, J=9.6 Hz, 6.4 Hz), 4.07 (dd, 1H, J=10 Hz, 3.2 Hz), 4.97 (br s, 1H), 6.93 (t, 1H, J=7.2 Hz), 7.03 (d, 1H, J=7.6 Hz), 7.12 (d, 1H, J=7.2 Hz), 7.67 (s, 1H), 7.70 (s, 1H), 8.03 (s, 1H), 12.01 (br s, 1H).

Workup

  1. distillationThe solvent was distilled off
  2. extractionthe product was extracted with EtOAc (3×15 mL)
  3. washThe combined organic extracts were washed with brine
  4. customdried
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-38a938eb36d1410d9b948597b924586a
Source dataset
uspto-grants-2014_05
Patent number
US08722720B2

Reaction notes

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