Sodium borohydride → HCID 66858297, compound

HRID 1888327Notes

Reaction equation

HRID 1888327 reaction equation
[OH:1][CH2:2][C@H:3]1[CH2:7][CH2:6][C:5](=[O:8])[N:4]1[CH2:9][C:10]1[S:11][CH:12]=[C:13](/[CH:15]=[CH:16]/[C:17]([O:19][CH2:20][CH2:21][CH2:22][CH3:23])=[O:18])[N:14]=1.[BH4-].[Na+]>O1CCCC1.C(O)CCC.C(OCC)(=O)C.O.O.O.O.O.O.[Ni](Cl)Cl>[OH:1][CH2:2][C@H:3]1[CH2:7][CH2:6][C:5](=[O:8])[N:4]1[CH2:9][C:10]1[S:11][CH:12]=[C:13]([CH2:15][CH2:16][C:17]([O:19][CH2:20][CH2:21][CH2:22][CH3:23])=[O:18])[N:14]=1

Participants

7

Reactant 2

HCID 4311764Sodium borohydrideHCID 66859694HCID 66859694, compound

Product 1

HCID 66858297HCID 66858297, compoundYield 69.3%

Reagents, catalysts & solvents 4

HCID 11791229Dichloronickel;hexahydrateCatalystHCID 2631-ButanolSolventHCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of the compound 74 (350 mg) in tetrahydrofuran (4.0 mL) and n-butanol (1.30 mL) was nickel chloride hexahydrate (246 mg) at room temperature and then thereto was added sodium borohydride (156 mg) at 0° C. The solution was stirred for 1 hour. The reaction solution was diluted with ethyl acetate and filtrated through Celite (Brand name). The obtained filtrate was washed an aqueous saturated ammonium chloride solution and brine, dried over anhydrous sodium sulfate and concentrated. The obtained residue was purified by column chromatography on silica gel (ethyl acetate:methanol=1:019:1) to give the title compound (244 mg) having the following physical data.

Workup

  1. customat room temperature
  2. filtrationfiltrated through Celite (Brand name)
  3. washThe obtained filtrate was washed an aqueous saturated ammonium chloride solution and brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. concentrationconcentrated
  6. customThe obtained residue was purified by column chromatography on silica gel (ethyl acetate:methanol=1:019:1)

Sources & evidence

ORD record
ord-9c03cd59ac59423fbc64dc428831ee65
Source dataset
uspto-grants-2013_08
Patent number
US08501793B2

Reaction notes

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