Sodium borohydride → HCID 57108405, compound

HRID 1252206Notes

Reaction equation

HRID 1252206 reaction equation
[BH4-].[Na+].[CH2:3]([CH:12]([CH2:25][C:26]1[CH:31]=[CH:30][C:29]([O:32][CH3:33])=[CH:28][CH:27]=1)[N:13]1[CH:16]([O:17][C:18](=[O:20])[CH3:19])[CH:15]([C:21](=[O:23])[CH3:22])[C:14]1=[O:24])[C:4]1[CH:9]=[CH:8][C:7]([O:10][CH3:11])=[CH:6][CH:5]=1>C(O)(C)C.O>[CH2:25]([CH:12]([CH2:3][C:4]1[CH:9]=[CH:8][C:7]([O:10][CH3:11])=[CH:6][CH:5]=1)[N:13]1[CH:16]([O:17][C:18](=[O:20])[CH3:19])[CH:15]([CH:21]([OH:23])[CH3:22])[C:14]1=[O:24])[C:26]1[CH:31]=[CH:30][C:29]([O:32][CH3:33])=[CH:28][CH:27]=1

Participants

5

Reactant 2

HCID 4311764Sodium borohydrideHCID 57097043HCID 57097043, compound

Product 1

HCID 57108405HCID 57108405, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 3776IsopropanolSolvent

Procedure

A mixture of sodium borohydride (38 mg) and 1-(di-p-anisylmethyl)-3-acetyl-4-acetoxy-2-azetidinone (397 mg) in isopropanol (6 ml) was stirred for 0.5 hour at room temperature. The reaction mixture was diluted with water and extracted with ethyl acetate. The extract was washed with water, dried over anhydrous sodium sulfate and evaporated to give 1-(di-p-anisylmethyl)-3-(1-hydroxyethyl)-4-acetoxy-2-azetidinone (the product was a mixture of two stereoisomers (about 1:1) of hydroxyethyl group).

Workup

  1. extractionextracted with ethyl acetate
  2. washThe extract was washed with water
  3. dry with materialdried over anhydrous sodium sulfate
  4. customevaporated

Sources & evidence

ORD record
ord-bf6e5099b9954d57b899102579e77b78
Source dataset
uspto-grants-1988_05
Patent number
US04742052

Reaction notes

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