Methanol → HCID 11543631, compound

HRID 2235282Notes

Reaction equation

HRID 2235282 reaction equation
[CH:1]1([N:7]2[CH2:11][CH2:10][CH:9]([CH2:12][C:13]3[CH:18]=[CH:17][CH:16]=[C:15]([O:19]C)[CH:14]=3)[C:8]2=[O:21])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.CC(=CC)C.CO.C(=O)(O)[O-].[Na+]>C(Cl)Cl>[CH:1]1([N:7]2[CH2:11][CH2:10][CH:9]([CH2:12][C:13]3[CH:18]=[CH:17][CH:16]=[C:15]([OH:19])[CH:14]=3)[C:8]2=[O:21])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6]1

Participants

6

Reactant 4

HCID 887MethanolHCID 105532-Methyl-2-buteneHCID 516892Sodium BicarbonateHCID 11572813HCID 11572813, compound

Product 1

HCID 11543631HCID 11543631, compoundYield 40.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Dissolve 1-cyclohexyl-3-(3-methoxy-benzyl)-pyrrolidin-2-one (example 67) (440 mg, 1.5 mmol) in methylene chloride (50 ml) and add 2-methyl 2-butene (0.97 ml, 9.2 mmol) followed by borontribromide (0.43 ml, 4.6 mmol) and stir at room temperature for 20 minutes. Pour reaction mixture into an ice, methanol, sodium bicarbonate mixture and stir for 5 minutes. Separate layers wash organic with brine dry over sodium sulfate, filter and concentrate. Purify by silica gel (10-20% ethyl acetate in hexanes) to yield 165 mg (39%) of the title compound: Mass spectrum (apci) m/z=274 (M+H).

Workup

  1. additionPour
  2. stirringstir for 5 minutes
  3. washSeparate layers wash organic with brine
  4. dry with materialdry over sodium sulfate
  5. filtrationfilter
  6. concentrationconcentrate
  7. customPurify by silica gel (10-20% ethyl acetate in hexanes)

Sources & evidence

ORD record
ord-88a803aaf645456aadd3f10c74fa2ce9
Source dataset
uspto-grants-2010_05
Patent number
US07713979B2

Reaction notes

Loading…