Sodium borohydride → (3S,4S)-4-(1-benzyloxycarbonylethyl)-3-(1-(R)-benzyloxycarbonyloxyethyl)-1-di(p-anisyl)methyl-2-azetidinone

HRID 1196220Notes

Reaction equation

HRID 1196220 reaction equation
[CH2:1]([O:8][C:9]([C:11]([C@H:13]1[N:16]([CH:17]([CH2:27][C:28]2[CH:33]=[CH:32][C:31]([O:34][CH3:35])=[CH:30][CH:29]=2)[CH2:18][C:19]2[CH:24]=[CH:23][C:22]([O:25][CH3:26])=[CH:21][CH:20]=2)[C:15](=[O:36])[C@@H:14]1[C@H:37]([O:39][C:40]([O:42][CH2:43][C:44]1[CH:49]=[CH:48][CH:47]=[CH:46][CH:45]=1)=[O:41])[CH3:38])=[CH2:12])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[BH4-].[Na+]>CO.C(OCC)(=O)C.[Ni](Cl)Cl>[CH2:1]([O:8][C:9]([CH:11]([C@H:13]1[N:16]([CH:17]([CH2:27][C:28]2[CH:29]=[CH:30][C:31]([O:34][CH3:35])=[CH:32][CH:33]=2)[CH2:18][C:19]2[CH:24]=[CH:23][C:22]([O:25][CH3:26])=[CH:21][CH:20]=2)[C:15](=[O:36])[C@@H:14]1[C@H:37]([O:39][C:40]([O:42][CH2:43][C:44]1[CH:49]=[CH:48][CH:47]=[CH:46][CH:45]=1)=[O:41])[CH3:38])[CH3:12])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 2

HCID 4311764Sodium borohydrideHCID 67919445(3S,4S)-4-(1-benzyloxycarbonylethenyl)-3-(1-(R)-benzyloxycarbonyloxyethyl)-1-di(p-anisyl)methyl-2-azetidinone

Product 1

HCID 67919668(3S,4S)-4-(1-benzyloxycarbonylethyl)-3-(1-(R)-benzyloxycarbonyloxyethyl)-1-di(p-anisyl)methyl-2-azetidinone

Reagents, catalysts & solvents 3

HCID 24385Nickel DichlorideCatalystHCID 887MethanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

A solution of (3S,4S)-4-(1-benzyloxycarbonylethenyl)-3-(1-(R)-benzyloxycarbonyloxyethyl)-1-di(p-anisyl)methyl-2-azetidinone (63 mg) in methanol (1.5 ml) was treated with sodium borohydride (7.7 mg) in the presence of nickel chloride (1.3 mg) at 0°-5° C. for 15 minutes. After stirring at room temperature for an additional 1 hour, the reaction mixture was diluted with ethyl acetate (30 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 thin-layer chromatography (SiO2) to yield (3S,4S)-4-(1-benzyloxycarbonylethyl)-3-(1-(R)-benzyloxycarbonyloxyethyl)-1-di(p-anisyl)methyl-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 thin-layer chromatography (SiO2)

Sources & evidence

ORD record
ord-1a75f19c0c6f442e989b533f5c947bdf
Source dataset
uspto-grants-1992_05
Patent number
US05112966

Reaction notes

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