Ammonium Chloride → HCID 67302996, compound

HRID 888896Notes

Reaction equation

HRID 888896 reaction equation
[CH3:1][C:2]1([CH3:23])[N:5]([CH2:6][C:7](OCC)=[O:8])[N:4]([CH:12]2[CH:19]3[CH2:20][CH:15]4[CH2:16][CH:17]([CH2:21][CH:13]2[CH2:14]4)[CH2:18]3)[C:3]1=[O:22].[BH4-].[Li+].[Cl-].[NH4+]>O1CCCC1CO.O>[CH3:1][C:2]1([CH3:23])[N:5]([CH2:6][CH2:7][OH:8])[N:4]([CH:12]2[CH:13]3[CH2:14][CH:15]4[CH2:16][CH:17]([CH2:18][CH:19]2[CH2:20]4)[CH2:21]3)[C:3]1=[O:22]

Participants

5

Reactant 3

HCID 25517Ammonium ChlorideHCID 4148881Lithium borohydrideHCID 86642248HCID 86642248, compound

Product 1

HCID 67302996HCID 67302996, compoundYield 124.6%

Reagents, catalysts & solvents 1

HCID 66577907Tetrahydrofuran-methanol waterSolvent

Procedure

Under an argon atmosphere, a mixed solution of ethyl [4,4-dimethyl-3-oxo-2-(adamantan-2-yl)-1,2-diazetidin-1-yl]acetate (150 mg, 0.470 mmol) in tetrahydrofuran-methanol-water (10:1:1, 4 mL) was added with lithium borohydride (80.8 mg, 3.76 mmol) at room temperature, and the resultant was stirred at the same temperature for 1 hour. The reaction solution was added with a saturated aqueous solution of ammonium chloride, and extracted with chloroform. The organic layer was dried over anhydrous sodium sulfate, concentrated in vacuo, the obtained residue was purified using silica gel chromatography (hexane:ethyl acetate=2:1), and 4,4-dimethyl-1-(2-hydroxyethyl)-2-(adamantan-2-yl)-1,2-diazetidin-3-one (163 mg, 78.7%) 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-27cc1e94f028463ea754b3e3054b73f0
Source dataset
uspto-grants-2012_08
Patent number
US08252781B2

Reaction notes

Loading…