Methyl iodide → HCID 70101951, compound

HRID 1780438Notes

Reaction equation

HRID 1780438 reaction equation
[CH3:1][C:2]1[CH:3]=[C:4]([C:7]2[CH:22]=[CH:21][C:10]3[C@:11]4([CH3:20])[C@@H:16]([CH2:17][CH2:18][C:9]=3[CH:8]=2)[NH:15][C:14](=[O:19])[CH2:13][CH2:12]4)[S:5][CH:6]=1.[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:4]4[S:5][CH:6]=[C:2]([CH3:1])[CH:3]=4)=[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 70273751HCID 70273751, compound

Product 1

HCID 70101951HCID 70101951, compoundYield 72%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

A 15 mL round bottom flask was charged with (+)-(4aR)-(10bR)-8-(4-methylthiophenyl)-10b-methyl-1,2,3,4,4a,5,6,10b-octahydrobenzo[f]quinolin-3-one (20 mg, 0.06 mmol), 0.10 mL of t-butanol, and potassium t-butoxide (20 mg, 0.18 mmol). Methyl iodide (0.011 mL, 0.18 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 (72%) of the title compound as a white solid. mp 115°-117°. FDMS: m/e=351.

Workup

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

Sources & evidence

ORD record
ord-a9929d9852cd4a4795aa31ee28208be9
Source dataset
uspto-grants-1997_05
Patent number
US05629007

Reaction notes

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