Methyl iodide → HCID 22877092, compound

HRID 1780440Notes

Reaction equation

HRID 1780440 reaction equation
[C:1]([C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[C:9]1[CH:24]=[CH:23][C:12]2[C@:13]3([CH3:22])[C@@H:18]([CH2:19][CH2:20][C:11]=2[CH:10]=1)[NH:17][C:16](=[O:21])[CH2:15][CH2:14]3)#[N:2].[C:25](O)(C)(C)C.CC(C)([O-])C.[K+].CI>C(OCC)(=O)C>[CH3:25][N:17]1[C@H:18]2[C@@:13]([CH3:22])([C:12]3[CH:23]=[CH:24][C:9]([C:4]4[CH:5]=[CH:6][CH:7]=[CH:8][C:3]=4[C:1]#[N:2])=[CH:10][C:11]=3[CH2:20][CH2:19]2)[CH2:14][CH2:15][C:16]1=[O:21]

Participants

6

Reactant 4

HCID 6328Methyl iodideHCID 6386tert-ButanolHCID 23665647Potassium tert-butoxideHCID 54041620HCID 54041620, compound

Product 1

HCID 22877092HCID 22877092, compoundYield 87%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

A 15 mL round bottom flask was charged with (+)-(4aR)-(10bR)-8-(2-cyanophenyl)-10b-methyl-1,2,3,4,4a,5,6,10b-octahydrobenzo[f]quinolin-3-one (55 mg, 0.17 mmol), 0.4 mL of t-butanol, and potassium t-butoxide (58 mg, 0.51 mmol). Methyl iodide (0.034 mL, 0.54 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 50 mg (87%) of the title compound as a white solid. mp 54°-55°. FDMS: m/e=330. α[D]589 =+74.33 (c=0.36, chloroform).

Workup

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

Sources & evidence

ORD record
ord-befd340bc9814c409ef76bc2ff0d610e
Source dataset
uspto-grants-1997_05
Patent number
US05629007

Reaction notes

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