Allyl bromide → HCID 19705450, compound

HRID 727539Notes

Reaction equation

[CH3:1][CH:2]([CH3:14])[CH2:3][CH:4]1[CH2:8][CH2:7][N:6]([Si](C)(C)C)[C:5]1=[O:13].[Li+].[CH3:16][CH:17]([N-]C(C)C)[CH3:18].C(Br)C=C>C1COCC1>[CH3:1][CH:2]([CH3:14])[CH2:3][C:4]1([C:17]([CH3:18])=[CH2:16])[CH2:8][CH2:7][NH:6][C:5]1=[O:13]

Participants

Conditions

Temperature: -78 °C

Procedure

A solution of 3-(2-methylpropyl)-1-trimethylsilyl-2-pyrrolidinone (10.2 g, 47.8 mmol) and THF (153 mL) is cooled to -78° C., and LDA (2.0 M, 26.3 mL, 52.6 mmol) is added. The solution is stirred at -78° C. for 30 minutes and then allyl bromide (5.0 mL, 57 mmol) is added. The solution is allowed to warm to 5° C. over 2.5 hours, and is then stirred at 5° C. for 1 hour. After quenching with saturated aqueous ammonium chloride (25 mL), aqueous workup (EtOAc, MgSO4) and purification by column chromatography (1:9:10 v/v CH2Cl2 :EtOAc:hexane) provides 7.76 g (90%) of the title compound as an oil.

Workup

temperatureto warm to 5° C. over 2.5 hours
stirringis then stirred at 5° C. for 1 hour
customAfter quenching with saturated aqueous ammonium chloride (25 mL), aqueous workup (EtOAc, MgSO4) and purification by column chromatography (1:9:10 v/v CH2Cl2 :EtOAc:hexane)

Sources & evidence

ORD record: ord-5aaa048104574debaf0d8af9dff79f49
Source dataset: uspto-grants-1998_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05712300

Reaction notes

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