Dimethylformamide → (R)-1-(5-Benzyloxypentyl)-4-butylpyrrolidin-2-one

HRID 2182490Notes

Reaction equation

[H-].[Na+].[CH2:3]([O:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15]Br)[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.[CH3:17][N:18](C)[CH:19]=[O:20]>C(OCC)(=O)C>[CH2:3]([O:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][N:18]1[CH2:17][C@H:9]([CH2:4][CH2:5][CH2:6][CH3:7])[CH2:8][C:19]1=[O:20])[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1

Participants

Conditions

Temperature: 0 °C

Procedure

To a solution of the compound of Example 2(c) (0.42 g, 2.9 mmol) in dry dimethylformamide (10 mL) under argon was slowly added sodium hydride (60% in mineral oil, 0.14 g, 3.5 mmol) at 0° C. After stirring at 0° C. for 30 minutes, 5-benzyloxypentyl bromide (0.9 g, 3.5 mmol) was dropwise added. The resulting mixture was stirred at room temperature overnight and then diluted with ethyl acetate (50 mL). The organic solution was washed with water (4×30 mL), brine (30 mL), dried (Na2SO4) and concentrated. The residue was purified by flash column chromatography (silica gel, 1:1 EtOAc/hexanes) to afford 0.73 g (95%) of the title compound as a clear oil: 1H NMR (CDCl3) δ 7.33 (m, 5H), 4.51 (s, 2H), 3.45 (m, 3H), 3.27 (t, 2H), 2.99 (dd, 1H), 2.52 (dd, 1H), 2.32 (m, 1H), 2.06 (m, 1H), 1.24-1.71 (m, 12H), 0.93 (t, 3H). MS(ES) m/e 318 [M+H]+.

Workup

customat 0° C
stirringThe resulting mixture was stirred at room temperature overnight
washThe organic solution was washed with water (4×30 mL), brine (30 mL)
dry with materialdried (Na2SO4)
concentrationconcentrated
customThe residue was purified by flash column chromatography (silica gel, 1:1 EtOAc/hexanes)

Sources & evidence

ORD record: ord-4ad46a424ae546fe8e44a339b4f35187
Source dataset: uspto-grants-2005_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06897233B2

Reaction notes

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