Methanol → 1-Cyclohexyl-4-dimethylamino-2-phenyl-2-buten-1-ol

HRID 845147Notes

Reaction equation

HRID 845147 reaction equation
[BH4-].[Na+].[C:3]1([CH:9]2[C:13]([C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=3)=[CH:12][CH:11]([NH:20][CH3:21])[O:10]2)[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.[CH3:22]O>>[CH:3]1([CH:9]([OH:10])[C:13]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)=[CH:12][CH2:11][N:20]([CH3:21])[CH3:22])[CH2:8][CH2:7][CH2:6][CH2:5][CH2:4]1

Participants

4

Reactant 3

HCID 887MethanolHCID 4311764Sodium borohydrideHCID 201336832,3-Diphenyl-5-methylamino-2,5-dihydrofuran

Product 1

HCID 538458471-Cyclohexyl-4-dimethylamino-2-phenyl-2-buten-1-ol

Conditions

Temperature
20 °C

Procedure

Sodium borohydride (10.3 g) is added over approximately 30 minutes at a temperature in the region of 5° C. to a solution of 2,3-diphenyl-5-methylamino-2,5-dihydrofuran (9.7 g) in methanol (90 cc) and distilled water (10 cc). The reaction mixture is then stirred for 18 hours at a temperature in the region of 20° C., and then concentrated to dryness under reduced pressure (2.7 kPa) at 40° C. The residue obtained is triturated with methylene chloride (100 cc); the suspension obtained is filtered and the filtrate is concentrated to dryness under reduced pressure (2.7 kPa) at 40° C. The residue is purified by chromatography on silica gel (400 g) in a 4 cm diameter column [eluent: methanol/aqueous ammonia (98/2 by volume)]. Elution is first carried out with solvent (400 cc); the corresponding eluate is discarded; elution then continues with solvent (600 cc); the corresponding eluate is concentrated to dryness under reduced pressure (2.7 kPa) at 40° C. The residue obtained is recrystallised from a mixture of hexane (70 cc) and isopropanol (10 cc). In this way 1,2-diphenyl-4-methylamino-2-buten-1-ol (Z) (3.8 g) is obtained in the form of white crystals melting at 90° C.

Workup

  1. distillationdistilled water (10 cc)
  2. concentrationconcentrated to dryness under reduced pressure (2.7 kPa) at 40° C
  3. customThe residue obtained
  4. customis triturated with methylene chloride (100 cc)
  5. customthe suspension obtained
  6. filtrationis filtered
  7. concentrationthe filtrate is concentrated to dryness under reduced pressure (2.7 kPa) at 40° C
  8. customThe residue is purified by chromatography on silica gel (400 g) in a 4 cm diameter column [eluent: methanol/aqueous ammonia (98/2 by volume)]
  9. washElution
  10. washelution
  11. concentrationthe corresponding eluate is concentrated to dryness under reduced pressure (2.7 kPa) at 40° C
  12. customThe residue obtained
  13. customis recrystallised from a mixture of hexane (70 cc) and isopropanol (10 cc)

Sources & evidence

ORD record
ord-11635eaaa8694519b666821ede155c51
Source dataset
uspto-grants-1988_07
Patent number
US04755599

Reaction notes

Loading…