tert-Butyl bromoacetate → tert-Butyl 3-(2-Methylpropyl)-2-oxo-1-(2-phenylethyl)-3-pyrrolidineacetate

HRID 727520Notes

Reaction equation

[Li+].CC([N-]C(C)C)C.[CH3:9][CH:10]([CH3:26])[CH2:11][CH:12]1[CH2:16][CH2:15][N:14]([CH2:17][CH2:18][C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[C:13]1=[O:25].Br[CH2:28][C:29]([O:31][C:32]([CH3:35])([CH3:34])[CH3:33])=[O:30]>C1COCC1>[CH3:9][CH:10]([CH3:26])[CH2:11][C:12]1([CH2:28][C:29]([O:31][C:32]([CH3:35])([CH3:34])[CH3:33])=[O:30])[CH2:16][CH2:15][N:14]([CH2:17][CH2:18][C:19]2[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=2)[C:13]1=[O:25]

Participants

Conditions

Temperature: -78 °C

Procedure

LDA (2.0M, 11.5 mL, 23.0 mmol) is added to a solution of 3-(2-methylpropyl)-1-(2-phenylethyl)-2-pyrrolidinone (4.70 g, 19.2 mmol) and THF (80 mL) at -78° C. The solution is stirred at -78° C. for 45 minutes, and tert-butyl bromoacetate (3.4 mL, 23 mmol) is added. The solution is allowed to warm to 0° C. over 2 hours and is allowed to stir overnight at room temperature. After quenching with saturated aqueous ammonium chloride, aqueous workup (EtOAc, MgSO4) and purification by column chromatography (10% EtOAc/5% CH2Cl2 /hexane) to give 4.67 g (68%) of the title compound as a colorless oil. An analytical sample is crystallized from hexane (mp 50° C.).

Workup

temperatureto warm to 0° C. over 2 hours
stirringto stir overnight at room temperature
customAfter quenching with saturated aqueous ammonium chloride, aqueous workup (EtOAc, MgSO4) and purification by column chromatography (10% EtOAc/5% CH2Cl2 /hexane)

Sources & evidence

ORD record: ord-04b6e3bf53124f07bdce32d0d4a41931
Source dataset: uspto-grants-1998_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05712300

Reaction notes

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