Methyl iodide → HCID 53936244, compound

HRID 1379494Notes

Reaction equation

HRID 1379494 reaction equation
[N+:1]([C:4]1[CH:9]=[C:8]([C:10]([F:13])([F:12])[F:11])[CH:7]=[CH:6][C:5]=1[C:14]1[CH:29]=[CH:28][C:17]2[C@:18]3([CH3:27])[C@@H:23]([CH2:24][CH2:25][C:16]=2[CH:15]=1)[NH:22][C:21](=[O:26])[CH2:20][CH2:19]3)([O-:3])=[O:2].[C:30](O)(C)(C)C.CC(C)([O-])C.[K+].CI>C(OCC)(=O)C>[CH3:30][N:22]1[C@H:23]2[C@@:18]([CH3:27])([C:17]3[CH:28]=[CH:29][C:14]([C:5]4[CH:6]=[CH:7][C:8]([C:10]([F:11])([F:12])[F:13])=[CH:9][C:4]=4[N+:1]([O-:3])=[O:2])=[CH:15][C:16]=3[CH2:25][CH2:24]2)[CH2:19][CH2:20][C:21]1=[O:26]

Participants

6

Reactant 4

HCID 6328Methyl iodideHCID 6386tert-ButanolHCID 23665647Potassium tert-butoxideHCID 54118905HCID 54118905, compound

Product 1

HCID 53936244HCID 53936244, compoundYield 76%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

A 15 mL round bottom flask was charged with (+)-(4aR)-(10bR)-8-(2-nitro-4-trifluoromethylphenyl)-10b-methyl-1,2,3,4,4a,5,6,10b-octahydrobenzo[f]quinolin-3-one (48 mg, 0.12 mmol), 0.3 mL of t-butanol, and potassium t-butoxide (40 mg, 0.36 mmol). Methyl iodide (0.022 mL, 0.36 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 38 mg (76%) of the title compound as an off-white solid. mp 55°-57°. FDMS: m/e =418. α[D]589 =+60.50 (c=0.16, methanol).

Workup

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

Sources & evidence

ORD record
ord-d5bdafa0ca3e4b9ba6dc6df25ceeabce
Source dataset
uspto-grants-1997_09
Patent number
US05670514

Reaction notes

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