Sodium borohydride → HCID 22841887, compound

HRID 1196219Notes

Reaction equation

HRID 1196219 reaction equation
[CH2:1]([O:3][C:4]([C:6]([C@H:8]1[NH:11][C:10](=[O:12])[C@@H:9]1[C@H:13]([O:15][C:16]([O:18][CH2:19][C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)=[O:17])[CH3:14])=[CH2:7])=[O:5])[CH3:2].[BH4-].[Na+]>C(O)(C)C.O.C(OCC)(=O)C.[Ni](Cl)Cl>[CH2:1]([O:3][C:4]([CH:6]([C@H:8]1[NH:11][C:10](=[O:12])[C@@H:9]1[C@H:13]([O:15][C:16]([O:18][CH2:19][C:20]1[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=1)=[O:17])[CH3:14])[CH3:7])=[O:5])[CH3:2]

Participants

7

Reactant 2

HCID 4311764Sodium borohydrideHCID 22841886HCID 22841886, compound

Product 1

HCID 22841887HCID 22841887, compound

Reagents, catalysts & solvents 4

HCID 24385Nickel DichlorideCatalystHCID 962WaterSolventHCID 3776IsopropanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

A solution of (3S,4S)-4-(1-ethoxycarbonylethenyl)-3-(1-(R)-benzyloxycarbonyloxyethyl)-2-azetidinone (1.04 g) in isopropanol (20 ml) and water (10 ml) was treated with sodium borohydride (230 mg) in the presence of nickel chloride (40 mg) at 0°-5° C. for 15 minutes. After stirring at room temperature for additional 1 hour, the reaction mixture was diluted with ethyl acetate (300 ml), washed with brine and dried over anhydrous sodium sulfate. Filtration and concentration of the filtrate in vacuo gave an oily residue, which was purified by silica gel chromatography to yield (3S,4S)-4-(1-ethoxycarbonylethyl)-3-(1-(R)-benzyloxycarbonyloxyethyl)-2-azetidinone.

Workup

  1. washwashed with brine
  2. dry with materialdried over anhydrous sodium sulfate
  3. filtrationFiltration and concentration of the filtrate in vacuo
  4. customgave an oily residue, which
  5. customwas purified by silica gel chromatography

Sources & evidence

ORD record
ord-cc5912e704cb4b54ab7338e1e13fcf8d
Source dataset
uspto-grants-1992_05
Patent number
US05112966

Reaction notes

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