Methyl iodide → HCID 70102381, compound

HRID 1780441Notes

Reaction equation

HRID 1780441 reaction equation
[CH3:1][C:2]1[S:3][CH:4]=[CH:5][C:6]=1[C:7]1[CH:22]=[CH:21][C:10]2[C@:11]3([CH3:20])[C@@H:16]([CH2:17][CH2:18][C:9]=2[CH:8]=1)[NH:15][C:14](=[O:19])[CH2:13][CH2:12]3.[C:23](O)(C)(C)C.CC(C)([O-])C.[K+].CI>C(OCC)(=O)C>[CH3:23][N:15]1[C@H:16]2[C@@:11]([CH3:20])([C:10]3[CH:21]=[CH:22][C:7]([C:6]4[CH:5]=[CH:4][S:3][C:2]=4[CH3:1])=[CH:8][C:9]=3[CH2:18][CH2:17]2)[CH2:12][CH2:13][C:14]1=[O:19]

Participants

6

Reactant 4

HCID 6328Methyl iodideHCID 6386tert-ButanolHCID 23665647Potassium tert-butoxideHCID 70273699HCID 70273699, compound

Product 1

HCID 70102381HCID 70102381, compoundYield 26%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

A 15 mL round bottom flask was charged with (+)-(4aR)-(10bR)-8-(2-methylthiophenyl)-10b-methyl-1,2,3,4,4a,5,6,10b-octahydrobenzo[f]quinolin-3-one (55 mg, 0.16 mmol), 0.4 mL of t-butanol, and potassium t-butoxide (55 mg, 0.48 mmol). Methyl iodide (0.031 mL, 0.48 mmol) was added and the mixture was stirred at room temperature for 4 h. The mixture was diluted with ethyl acetate, and purified by silica gel chromatography (ethyl acetate eluent) to give 15 mg (26%) of the title compound as an oil. FDMS: m/e=351.

Workup

  1. custompurified by silica gel chromatography (ethyl acetate eluent)

Sources & evidence

ORD record
ord-c222bdb4e8cf4a87abed09317ee3d154
Source dataset
uspto-grants-1997_05
Patent number
US05629007

Reaction notes

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