Methyl iodide → HCID 67305534, compound

HRID 1009819Notes

Reaction equation

HRID 1009819 reaction equation
Cl([O-])(=O)(=O)=O.[Li+].O=[C:8]1[CH2:32][C@@H:31]2[C@@H:10]([C:11]3[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=3[C:17]3([CH2:30]2)[CH2:22][CH2:21][N:20]([C:23]([O:25][C:26]([CH3:29])([CH3:28])[CH3:27])=[O:24])[CH2:19][CH2:18]3)[NH:9]1.[CH3:33]I>C1COCC1>[CH3:33][N:9]1[C@H:10]2[C@H:31]([CH2:30][C:17]3([C:12]4[CH:13]=[CH:14][CH:15]=[CH:16][C:11]=42)[CH2:18][CH2:19][N:20]([C:23]([O:25][C:26]([CH3:28])([CH3:29])[CH3:27])=[O:24])[CH2:21][CH2:22]3)[CH2:32][CH2:8]1

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 23665649Lithium perchlorateHCID 57659372HCID 57659372, compound

Product 1

HCID 67305534HCID 67305534, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Sodium hydride (60% dispersed in oil, 58 mg) was washed with anhydrous 2,2,4-trimethylpentane and suspended in anhydrous THF. Lithium perchlorate (78 mg, 0.73 mmol) was added to the suspension at 0° C., followed by (3aR,9bS)-tert-butyl 2-oxo-1,2,3,3a,4,9b-hexahydrospiro[benzo[g]indole-5,4′-piperidine]-1′-carboxylate (142 mg, 0.4 mmol) in THF (10 ml) at 0° C. After 15 min, methyl iodide (0.04 ml, 0.6 mmol) was added. The reaction mixture was stirred at room temperature for 1 h then heated under reflux for 1 h. Concentration gave the title compound. LC-MS: m/e=371.6 (M+), 315.5 (M−tBu+1, 100%). Rt=3.12 min.

Workup

  1. washSodium hydride (60% dispersed in oil, 58 mg) was washed with anhydrous 2,2,4-trimethylpentane
  2. temperaturethen heated
  3. temperatureunder reflux for 1 h
  4. concentrationConcentration

Sources & evidence

ORD record
ord-a73912cff30249ccb9fe6b49f129f1d0
Source dataset
uspto-grants-2011_07
Patent number
US07973162B2

Reaction notes

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