HCID 18768988, compound → HCID 18768982, compound

HRID 480244Notes

Reaction equation

[CH2:1]([N:8]([CH3:16])[CH2:9][C:10](N(OC)C)=[O:11])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH2:17]([Mg]Cl)[CH2:18][C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1>C1COCC1>[CH2:1]([N:8]([CH3:16])[CH2:9][C:10](=[O:11])[CH2:17][CH2:18][C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

Conditions

Temperature: -78 °C

Procedure

2-(Benzyl-methyl-amino)-N-methoxy-N-methyl-acetamide (2.0 g, 9.0 mmol, 1.0 equiv) was dissolved in 30 mL of dry THF under argon. The solution was cooled to −78° C. and a 1 M solution of phenethyl magnesium chloride (12.6 mL, 12.6 mmol, 1.4 equiv) was added dropwise of a period of 1 min. The resulting mixture was stirred at −78° C. for 3 h, warmed to 0° C. for 20 min and recooled to −78° C. at which time the reaction was quenched by the addition of 5 mL of saturated sodium bicarbonate. The reaction solution was diluted with 200 mL of EtOAc and 200 mL of water. The layers were separated and the organic layer was dried over Na2SO4, decanted and concentrated to an oil (2.4 g, ˜100%) which was used without further purification; MS, m/z 268=M+1.

Workup

temperaturewarmed to 0° C. for 20 min
customrecooled to −78° C. at which time
customwas quenched by the addition of 5 mL of saturated sodium bicarbonate
additionThe reaction solution was diluted with 200 mL of EtOAc and 200 mL of water
customThe layers were separated
dry with materialthe organic layer was dried over Na2SO4
customdecanted
concentrationconcentrated to an oil (2.4 g, ˜100%) which
customwas used without further purification

Sources & evidence

ORD record: ord-94ef2053d045457f81242c610e866cd6
Source dataset: uspto-grants-2003_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06649642B2

Reaction notes

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