Acetic Acid → HCID 46194512, compound

HRID 888889Notes

Reaction equation

HRID 888889 reaction equation
[CH:1]12[CH2:10][CH:5]3[CH2:6][CH:7]([CH2:9][CH:3]([CH2:4]3)[CH:2]1[N:11]1[C:14](=[O:15])[C:13]([CH3:17])([CH3:16])[NH:12]1)[CH2:8]2.[C:18]1([CH2:24][CH:25]=O)[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].C(O)(=O)C>C(Cl)(Cl)Cl.O>[CH3:16][C:13]1([CH3:17])[N:12](/[CH:25]=[CH:24]/[C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[N:11]([CH:2]2[CH:3]3[CH2:4][CH:5]4[CH2:6][CH:7]([CH2:8][CH:1]2[CH2:10]4)[CH2:9]3)[C:14]1=[O:15]

Participants

7

Reactant 4

HCID 176Acetic AcidHCID 998PhenylacetaldehydeHCID 5049666Sodium triacetoxyborohydrideHCID 673028822-(Adamantan-2-yl)-4,4-dimethyl-1,2-diazetidin-3-one

Product 1

HCID 46194512HCID 46194512, compoundYield 5.2%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6212ChloroformSolvent

Procedure

A solution of 2-(adamantan-2-yl)-4,4-dimethyl-1,2-diazetidin-3-one (50.0 mg, 0.213 mmol) prepared in Process 3 of Example 12 in chloroform (3 mL) was added sequentially with phenylacetaldehyde (25.6 mg, 0.213 mmol), sodium triacetoxyborohydride (67.8 mg, 0.320 mmol) and acetic acid (15.4 mg, 0.256 mmol) at room temperature, and the resultant was stirred at the same temperature for 2 hours. The reaction solution was added with water and extracted with chloroform. The organic layer was dried over anhydrous sodium sulfate, concentrated in vacuo, the obtained residue was purified using Preparatory Thin-Layer chromatography (hexane:ethyl acetate=4:1), and the title compound (3.70 mg, 5.20%) was obtained as a colorless oil.

Workup

  1. extractionextracted with chloroform
  2. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  3. concentrationconcentrated in vacuo
  4. customthe obtained residue was purified

Sources & evidence

ORD record
ord-d0454a46bfe64197a3f6a207fcadd59a
Source dataset
uspto-grants-2012_08
Patent number
US08252781B2

Reaction notes

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