Hydrochloric Acid → [1-(4-Fluoro-phenyl)-4-hydroxy-cyclohexyl]-carbamic acid benzyl ester

HRID 2370297Notes

Reaction equation

HRID 2370297 reaction equation
[CH2:1]([O:8][C:9](=[O:25])[NH:10][C:11]1([C:18]2[CH:23]=[CH:22][C:21]([F:24])=[CH:20][CH:19]=2)[CH2:16][CH2:15][C:14](=[O:17])[CH2:13][CH2:12]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[BH4-].[Na+].O.Cl>C1COCC1>[CH2:1]([O:8][C:9](=[O:25])[NH:10][C:11]1([C:18]2[CH:23]=[CH:22][C:21]([F:24])=[CH:20][CH:19]=2)[CH2:16][CH2:15][CH:14]([OH:17])[CH2:13][CH2:12]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 4311764Sodium borohydrideHCID 59226032[1-(4-Fluoro-phenyl)-4-oxo-cyclohexyl]-carbamic acid benzyl ester

Product 1

HCID 59226075[1-(4-Fluoro-phenyl)-4-hydroxy-cyclohexyl]-carbamic acid benzyl esterYield 91.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

1.5 g of [1-(4-Fluoro-phenyl)-4-oxo-cyclohexyl]-carbamic acid benzyl ester (77) were dissolved in 30 mL of dry THF and 182 mg of sodium borohydride were added. When conversion was complete, the mixture was poured into 15 mL of water. pH was adjusted to 2 by addition of 2N HCl and the aqueous layer was extracted with ethyl acetate. The combined organic layer was extracted with brine, dried over magnesium sulfate and evaporated to dryness to give 1.38 g of the desired product as a mixture of cis and trans isomers, the cis isomer (referring to the position of alcohol and Z-amine) being the major one. Rt=2.20 min (Method E). Detected mass: 344.2 (M+H+).

Workup

  1. extractionthe aqueous layer was extracted with ethyl acetate
  2. extractionThe combined organic layer was extracted with brine
  3. dry with materialdried over magnesium sulfate
  4. customevaporated to dryness

Sources & evidence

ORD record
ord-644bf06191cc4b31b01dc811659c6e09
Source dataset
uspto-grants-2014_04
Patent number
US08710077B2

Reaction notes

Loading…