Ammonium Chloride → 3-Benzyl-4-hydroxy-4-methyl-3-azabicyclo[3.1.0]hexan-2-one

HRID 2218236Notes

Reaction equation

HRID 2218236 reaction equation
[CH2:1]([N:8]1[C:13](=[O:14])[CH:12]2[CH:10]([CH2:11]2)[C:9]1=[O:15])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH3:16][Li].[Cl-].[NH4+]>O1CCCC1.CCOCC>[CH2:1]([N:8]1[C:13]([OH:14])([CH3:16])[CH:12]2[CH:10]([CH2:11]2)[C:9]1=[O:15])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 3

HCID 25517Ammonium ChlorideHCID 27645863-Benzyl-3-azabicyclo(3.1.0)hexane-2,4-dioneHCID 178418348HCID 178418348, compound

Product 1

HCID 691215203-Benzyl-4-hydroxy-4-methyl-3-azabicyclo[3.1.0]hexan-2-one

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-78 °C

Procedure

3-benzyl-3-azabicyclo[3.1.0]hexane-2,4-dione(U.S. Pat. No. 4,183,857, 1.9 gm, 9.5 mmol) was dissolved in 100 ml of tetrahydrofuran and cooled to −78° C. Methyllithium (10.5 ml of a 0.98M solution in ether, 10.2 mmol) was added dropwise. Saturated aqueous ammonium chloride was added to the cold reaction mixture; the mixture was then extracted with ethyl acetate. The combined organic layers were dried over sodium sulphate, filtered and concentrated in vacuo to provide the title compound.

Workup

  1. extractionthe mixture was then extracted with ethyl acetate
  2. dry with materialThe combined organic layers were dried over sodium sulphate
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-776635ea68804833a8ab108d727ea043
Source dataset
uspto-grants-2008_08
Patent number
US07410993B2

Reaction notes

Loading…