Methyl iodide → HCID 54182136, compound

HRID 1780446Notes

Reaction equation

HRID 1780446 reaction equation
[Cl:1][C:2]1[C:7]([F:8])=[C:6]([F:9])[C:5]([C:10]2[CH:25]=[CH:24][C:13]3[C@:14]4([CH3:23])[C@@H:19]([CH2:20][CH2:21][C:12]=3[CH:11]=2)[NH:18][C:17](=[O:22])[CH2:16][CH2:15]4)=[C:4]([F:26])[C:3]=1[F:27].[C:28](O)(C)(C)C.CC(C)([O-])C.[K+].CI>C(OCC)(=O)C>[CH3:28][N:18]1[C@H:19]2[C@@:14]([CH3:23])([C:13]3[CH:24]=[CH:25][C:10]([C:5]4[C:4]([F:26])=[C:3]([F:27])[C:2]([Cl:1])=[C:7]([F:8])[C:6]=4[F:9])=[CH:11][C:12]=3[CH2:21][CH2:20]2)[CH2:15][CH2:16][C:17]1=[O:22]

Participants

6

Reactant 4

HCID 6328Methyl iodideHCID 6386tert-ButanolHCID 23665647Potassium tert-butoxideHCID 54033273HCID 54033273, compound

Product 1

HCID 54182136HCID 54182136, compoundYield 66%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

A 15 mL round bottom flask was charged with (+)-(4aR)-(10bR)-8-(4-chloro-2,3,5,6-tetrafluorophenyl)-10b-methyl-1,2,3,4,4a,5,6,10b-octahydrobenzo[f]quinolin-3-one (43 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 30 mg (66%) of the title compound as an off-white solid. mp 150°-151°. FDMS: m/e=412 α[D]589 =+68.57 (c=0.12, chloroform).

Workup

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

Sources & evidence

ORD record
ord-7f1df5ed63134d4eb64aaa93572d3993
Source dataset
uspto-grants-1997_05
Patent number
US05629007

Reaction notes

Loading…