Ethanol → HCID 9841901, compound

HRID 266878Notes

Reaction equation

HRID 266878 reaction equation
[BH4-].[Na+].[Cl:3][C:4]1[CH:5]=[C:6]([C:11]2([C:15](=[O:24])[CH2:16][S:17][CH2:18][CH2:19][CH2:20][N:21]([CH3:23])[CH3:22])[CH2:14][CH2:13][CH2:12]2)[CH:7]=[CH:8][C:9]=1[Cl:10].C(O)C>CO.O>[Cl:3][C:4]1[CH:5]=[C:6]([C:11]2([CH:15]([OH:24])[CH2:16][S:17][CH2:18][CH2:19][CH2:20][N:21]([CH3:23])[CH3:22])[CH2:14][CH2:13][CH2:12]2)[CH:7]=[CH:8][C:9]=1[Cl:10]

Participants

6

Reactant 3

HCID 702Ethanol2×HCID 4311764Sodium borohydrideHCID 9863685HCID 9863685, compound

Product 1

HCID 9841901HCID 9841901, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

Sodium borohydride (3.2 g) was added in portions at 0° C. under nitrogen to a stirred solution of 1-[1-(3,4-dichlorophenyl)cyclobutyl]-2-[3-(dimethylamino)-propylthio]ethanone (16 g, prepared by basification of the hydrochloride salt obtained in a similar manner to that described in Example 7) in methanol (200 ml) then the mixture was stirred at ambient temperature for 7 days and diluted with water (350 ml). The product was extracted into dichloromethane (4×100 ml) and the extracts washed with water (100 ml) and saturated aqueous sodium chloride solution (100 ml), dried over sodium sulphate and the solvent removed in vacuo to leave a green oil. The oil was resolved via preparative scale chiral high performance liquid chromatography to give (-)-1-[1-(3,4-dichlorophenyl)cyclobutyl]-2-[3 -(dimethylamino)propylthio]ethanol as an oil (3.5 g), [α]rtD =-8.615° (C=1;ethanol) and (+)-1-[1-(3 4-dichlorophenyl)cyclobutyl]-2-[3-(dimethylamino) propylthio]ethanol as an oil (3.4 g), [α]rtD =+9.740° (C=1; ethanol).

Workup

  1. customobtained in a similar manner to that
  2. extractionThe product was extracted into dichloromethane (4×100 ml)
  3. washthe extracts washed with water (100 ml) and saturated aqueous sodium chloride solution (100 ml)
  4. dry with materialdried over sodium sulphate
  5. customthe solvent removed in vacuo
  6. customto leave a green oil

Sources & evidence

ORD record
ord-3cece3ecee46449d8c195a1489f91dcd
Source dataset
uspto-grants-1997_07
Patent number
US05652271

Reaction notes

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