Methyl iodide → Methyl 8-benzyl-3-(4-isopropoxy-3-methyl-benzoyl)-11-oxa-3,8-diazaspiro[5.5]undecane-10-carboxylate

HRID 713119Notes

Reaction equation

HRID 713119 reaction equation
[CH2:1]([N:8]1[CH2:31][CH:30]([C:32]([OH:34])=[O:33])[O:29][C:10]2([CH2:15][CH2:14][N:13]([C:16](=[O:28])[C:17]3[CH:22]=[CH:21][C:20]([O:23][CH:24]([CH3:26])[CH3:25])=[C:19]([CH3:27])[CH:18]=3)[CH2:12][CH2:11]2)[CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:35]([O-])([O-])=O.[K+].[K+].IC>CN(C=O)C.C(OCC)(=O)C>[CH2:1]([N:8]1[CH2:31][CH:30]([C:32]([O:34][CH3:35])=[O:33])[O:29][C:10]2([CH2:15][CH2:14][N:13]([C:16](=[O:28])[C:17]3[CH:22]=[CH:21][C:20]([O:23][CH:24]([CH3:25])[CH3:26])=[C:19]([CH3:27])[CH:18]=3)[CH2:12][CH2:11]2)[CH2:9]1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 3

HCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 708728658-Benzyl-3-(4-isopropoxy-3-methyl-benzoyl)-11-oxa-3,8-diazaspiro[5.5]undecane-10-carboxylic acid

Product 1

HCID 70872811Methyl 8-benzyl-3-(4-isopropoxy-3-methyl-benzoyl)-11-oxa-3,8-diazaspiro[5.5]undecane-10-carboxylateYield 104%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

8-Benzyl-3-(4-isopropoxy-3-methyl-benzoyl)-11-oxa-3,8-diazaspiro[5.5]undecane-10-carboxylic acid (10 mg, 0.02 mmol), K2CO3 (12 mg, 0.09 mmol) and iodomethane (2 μL, 0.03 mmol) in DMF (0.1 mL) was stirred for 1 hour. The mixture was diluted with ethyl acetate (5 mL), washed with water (2 mL) and brine (2 mL), dried over magnesium sulfate, filtered and evaporated to give methyl 8-benzyl-3-(4-isopropoxy-3-methyl-benzoyl)-11-oxa-3,8-diazaspiro[5.5]undecane-10-carboxylate (10 mg, 100%). ESI-MS m/z calc. 480.6. found 481.5 (M+1)+; Retention time: 1.82 minutes (3 min run).

Workup

  1. washwashed with water (2 mL) and brine (2 mL)
  2. dry with materialdried over magnesium sulfate
  3. filtrationfiltered
  4. customevaporated

Sources & evidence

ORD record
ord-bee3cd317b514c0db53d8751a3313f49
Source dataset
uspto-grants-2015_11
Patent number
US09181273B2

Reaction notes

Loading…