Sodium borohydride → HCID 178521561, compound

HRID 84306Notes

Reaction equation

HRID 84306 reaction equation
[Br:1][C:2]1[CH:18]=[CH:17][C:5]([O:6][C:7]([F:16])([F:15])[CH:8]2[CH2:13][CH2:12][C:11](=[O:14])[CH2:10][CH2:9]2)=[CH:4][CH:3]=1.[BH4-].[Na+]>C(O)C>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([O:6][C:7]([F:15])([F:16])[C@H:8]2[CH2:9][CH2:10][C@H:11]([OH:14])[CH2:12][CH2:13]2)=[CH:17][CH:18]=1

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 672502664-[(4-Bromo-phenoxy)-difluoro-methyl]-cyclohexanone

Product 1

HCID 178521561HCID 178521561, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
0 °C

Procedure

To a stirred solution of 4-[(4-bromo-phenoxy)-difluoro-methyl]-cyclohexanone (1050 mg, 3.290 mmoles) in ethanol (16.4 mL, 0.2M) was added NaBH4 (249 mg, 6.58 mmoles) 0° C. The solution was stirred at 0° C. for 20 minutes and then warmed to room temperature for 20 minutes. The reaction was quenched with 1 N HCl to a pH of ˜7, and extracted three times with ethyl acetate. The organics where combined, dried over magnesium sulfate, filtered and concentrated. Cis/trans isomers were then separated by chiral purification. Isolated 260 mg of trans isomer (24%). 1H NMR (400 MHz, METHANOL-d4) δ ppm 1.39 (s, 2 H) 1.51-1.65 (m, 2 H) 1.83-1.96 (m, 2 H) 2.01-2.21 (m, 2 H) 2.38-2.47 (m, 1 H) 7.03-7.14 (m, 2 H) 7.41-7.58 (m, 2 H)

Workup

  1. temperaturewarmed to room temperature for 20 minutes
  2. customThe reaction was quenched with 1 N HCl to a pH of ˜7
  3. extractionextracted three times with ethyl acetate
  4. dry with materialdried over magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customCis/trans isomers were then separated by chiral purification
  8. customIsolated 260 mg of trans isomer (24%)

Sources & evidence

ORD record
ord-fa629faf936e40789d6699c9df645c77
Source dataset
uspto-grants-2014_09
Patent number
US08846933B2

Reaction notes

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