Benzyl Bromide → HCID 19705487, compound

HRID 727542Notes

Reaction equation

[CH3:1][CH:2]([CH3:19])[CH2:3][C:4]1([C:16]([CH3:18])=[CH2:17])[CH2:8][CH2:7][N:6]([CH2:9][C:10]([O:12][CH2:13][CH3:14])=[O:11])[C:5]1=[O:15].[Li+].CC([N-]C(C)C)C.[CH2:28](Br)[C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1>C1COCC1>[CH3:19][CH:2]([CH3:1])[CH2:3][C:4]1([C:16]([CH3:18])=[CH2:17])[CH2:8][CH2:7][N:6]([CH:9]([CH2:28][C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=2)[C:10]([O:12][CH2:13][CH3:14])=[O:11])[C:5]1=[O:15]

Participants

Conditions

Temperature: -78 °C

Procedure

A solution of ethyl 3-(2-methylpropyl)-2-oxo-3-(propen-2-yl)-1-pyrrolidineacetate (Example 20, step 5; 1.63 g, 6.10 mmol) and THF (15 mL) is cooled to -78° C. and LDA (2.0M, 3.2 mL, 6.4 mmol) is added. The solution is stirred at -78° C. for 30 minutes and then benzyl bromide (0.80 mL, 6.7 mmol) is added. The solution is allowed to warm to 0° C. over 2 hours, and then stirred at 0° C. for 1 hour. After quenching with saturated aqueous ammonium chloride (10 mL), aqueous workup (EtOAc, MgSO4) and purification by column chromatography (10% EtOAc/hexane) provided 1.94 g (89%) of the title compound as an oil in a 1:1 mixture of diastereomers.

Workup

temperatureto warm to 0° C. over 2 hours
stirringstirred at 0° C. for 1 hour
customAfter quenching with saturated aqueous ammonium chloride (10 mL), aqueous workup (EtOAc, MgSO4) and purification by column chromatography (10% EtOAc/hexane)

Sources & evidence

ORD record: ord-e5c45772fe6c4e76a4c1c53ab17fb037
Source dataset: uspto-grants-1998_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05712300

Reaction notes

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