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

HRID 915262Notes

Reaction equation

HRID 915262 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 (Prepared as per 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-ab0a013d415a4bc682ea8d38df4f5433
Source dataset
uspto-grants-2007_09
Patent number
US07265147B2

Reaction notes

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