Ethyl bromoacetate → HCID 54302501, compound

HRID 727540Notes

Reaction equation

C[Si]([N-][Si](C)(C)C)(C)C.[K+].[CH3:11][CH:12]([CH3:23])[CH2:13][C:14]1([C:20]([CH3:22])=[CH2:21])[CH2:18][CH2:17][NH:16][C:15]1=[O:19].Br[CH2:25][C:26]([O:28][CH2:29][CH3:30])=[O:27]>C1COCC1>[CH3:11][CH:12]([CH3:23])[CH2:13][C:14]1([C:20]([CH3:22])=[CH2:21])[CH2:18][CH2:17][N:16]([CH2:25][C:26]([O:28][CH2:29][CH3:30])=[O:27])[C:15]1=[O:19]

Participants

Conditions

Temperature: 0 °C

Procedure

A solution of potassium bis(trimethylsilyl)amide (0.5M in toluene, 16.4 mL, 8.19 mmol) is cooled to 0° C., and a solution of 3-(2-methylpropyl)-3-(propen-2-yl)-2-pyrrolidinone (1.24 g, 6.82 mmol) in THF (10 mL) is added dropwise over 2 minutes After stirring at 0° C. for 40 minutes, ethyl bromoacetate (0.91 mL, 8.2 mmol) is added. The reaction is stirred at 0° C. for 3 hours and for 1 hour at room temperature. After quenching with saturated aqueous ammonium chloride (10 mL), aqueous workup (EtOAc, MgSO4) and purification by column chromatography (1:9:10 v/v CH2Cl2 :EtOAc:hexane) provided 1.66 g (91%) of the title compound as an oil.

Workup

stirringThe reaction is stirred at 0° C. for 3 hours and for 1 hour at room temperature
customAfter quenching with saturated aqueous ammonium chloride (10 mL), aqueous workup (EtOAc, MgSO4) and purification by column chromatography (1:9:10 v/v CH2Cl2 :EtOAc:hexane)

Sources & evidence

ORD record: ord-ad54349e99de4ccd9b673977ddf7b0d8
Source dataset: uspto-grants-1998_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05712300

Reaction notes

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