Methyl 1-(4-bromophenyl)cyclopropyl(3-oxo-3-phenylpropyl)carbamate → HCID 66870054, compound

HRID 1422653Notes

Reaction equation

HRID 1422653 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2([N:11]([CH2:16][CH2:17][C:18](=[O:25])[C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=3)[C:12](=[O:15])[O:13][CH3:14])[CH2:10][CH2:9]2)=[CH:4][CH:3]=1.[CH3:26][C:27](=[CH2:31])[CH2:28][Mg]Cl>C1COCC1>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2([N:11]([CH2:16][CH2:17][C:18]([OH:25])([C:19]3[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=3)[CH2:28][C:27]([CH3:31])=[CH2:26])[C:12](=[O:15])[O:13][CH3:14])[CH2:9][CH2:10]2)=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 66869637Methyl 1-(4-bromophenyl)cyclopropyl(3-oxo-3-phenylpropyl)carbamateHCID 178448200HCID 178448200, compound

Product 1

HCID 66870054HCID 66870054, compoundYield 41%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of methyl 1-(4-bromophenyl)cyclopropyl(3-oxo-3-phenylpropyl)carbamate (127 mg, 0.316 mmol) in dry THF (10 mL) was cooled to −78° C. A solution of 0.5M 2-methylallylmagnesium chloride in THF (1.9 mL, 3 equiv) was added. After 10min, the reaction mixture was warmed to rt slowly and stirred for 1 h. LC-MS found the reaction was complete. The mixture was quenched with satd aq NH4Cl (3 mL), diluted with ether (40 mL), washed with 1% aq HCl (8 mL), satd aq NaHCO3 (7 mL), and brine (5 mL), and dried over Na2SO4. After filtration and concentration, the residue was purified by chromatography on a 12-g silica gel column, eluted with a 0˜30% EtOAc in hexanes gradient, to afford methyl 1-(4-bromophenyl)cyclopropyl(3-hydroxy-5-methyl-3-phenylhex-5-enyl)carbamate (58.8 mg, 41%).

Workup

  1. customThe mixture was quenched with satd aq NH4Cl (3 mL)
  2. additiondiluted with ether (40 mL)
  3. washwashed with 1% aq HCl (8 mL)
  4. dry with materialdried over Na2SO4
  5. filtrationAfter filtration and concentration
  6. customthe residue was purified by chromatography on a 12-g silica gel column
  7. washeluted with a 0˜30% EtOAc in hexanes gradient

Sources & evidence

ORD record
ord-9438bba4ba6e41648c0e54607c2012aa
Source dataset
uspto-grants-2015_01
Patent number
US08927539B2

Reaction notes

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