Magnesium → (3S,5S)-3-(3,3-Dimethylbutyl)-3-methyl-5-phenylmorpholin-2-one

HRID 1433317Notes

Reaction equation

HRID 1433317 reaction equation
[Mg].I[CH2:3][CH2:4][C:5]([CH3:8])([CH3:7])[CH3:6].[CH3:9][C:10]1[C:11](=[O:22])[O:12][CH2:13][C@H:14]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[N:15]=1>O1CCCC1.C(OCC)C>[CH3:6][C:5]([CH3:8])([CH3:7])[CH2:4][CH2:3][C@@:10]1([CH3:9])[C:11](=[O:22])[O:12][CH2:13][C@H:14]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[NH:15]1

Participants

6

Reactant 3

HCID 5462224MagnesiumHCID 148248991-Iodo-3,3-dimethylbutaneHCID 57467834(5S)-3-methyl-5-phenyl-5,6-dihydro-2H-1,4-oxazin-2-one

Product 1

HCID 57935239(3S,5S)-3-(3,3-Dimethylbutyl)-3-methyl-5-phenylmorpholin-2-one

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent

Procedure

A suspension of Rieke Magnesium (343 mg, 14.1 mmol) in tetrahydrofuran (13.7 ml) was added to a solution of 1-iodo-3,3-dimethylbutane in diethylether (50 ml) over a period of twenty minutes and the reaction was stirred for 40 minutes at room temperature. The Grignard reagent solution and (5S)-3-methyl-5-phenyl-5,6-dihydro-2H-1,4-oxazin-2-one (1 g, 5.28 mmol, see WO-A-02/051983) were used according to the method of Preparation 1 to generate the title compound. The total amount of compound synthesised was 0.394 g.

Workup

  1. customwere used according to the method of Preparation 1

Sources & evidence

ORD record
ord-d4c0ca7f12de47db9aeae97cd3fff124
Source dataset
uspto-grants-2009_11
Patent number
US07612226B2

Reaction notes

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