Sodium borohydride → HCID 67075178, compound

HRID 45213Notes

Reaction equation

HRID 45213 reaction equation
[BH4-].[Na+].[C:3]([O:7][C:8](=[O:26])[NH:9][CH:10]([C:18]1[CH:23]=[CH:22][C:21]([O:24][CH3:25])=[CH:20][CH:19]=1)[CH:11]1[CH2:16][CH2:15][C:14](=[O:17])[CH2:13][CH2:12]1)([CH3:6])([CH3:5])[CH3:4]>CO.C1COCC1>[C:3]([O:7][C:8](=[O:26])[NH:9][CH:10]([CH:11]1[CH2:16][CH2:15][CH:14]([OH:17])[CH2:13][CH2:12]1)[C:18]1[CH:23]=[CH:22][C:21]([O:24][CH3:25])=[CH:20][CH:19]=1)([CH3:6])([CH3:4])[CH3:5]

Participants

5

Reactant 2

HCID 4311764Sodium borohydrideHCID 67075403HCID 67075403, compound

Product 1

HCID 67075178HCID 67075178, compound

Reagents, catalysts & solvents 2

HCID 887MethanolCatalystHCID 8028TetrahydrofuranSolvent

Procedure

Sodium borohydride (12 mg, 0.34 mmol) and 2 drops methanol were added to a solution of [(4-methoxy-phenyl)-(4-oxo-cyclohexyl)-methyl]-carbamic acid tert-butyl ester (33, 110 mg) in THF (5 mL). After stirring for 7 hours the reaction was worked up by washing the solution with saturated sodium bicarbonate solution and brine. After drying the organic phase over sodium sulphate, followed by filtration, evaporation gave 101 mg of the desired cis/trans isomer mixture (34) as a colourless solid, which was used directly in the next stage. Rt=1.36, 1.39 min (Method 5). Detected mass: 219.2 (M—C4H8—CO2—H2O+).

Workup

  1. washby washing the solution with saturated sodium bicarbonate solution and brine
  2. dry with materialAfter drying the organic phase over sodium sulphate
  3. filtrationfollowed by filtration, evaporation

Sources & evidence

ORD record
ord-5bd95f58e8c946ffaf1f670a019c3d13
Source dataset
uspto-grants-2013_09
Patent number
US08541449B2

Reaction notes

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