Allyl bromide → Ethyl 1-[(phenylmethoxy)carbonyl]-α-2-propen-1-yl-4-piperidineacetate

HRID 1664774Notes

Reaction equation

[CH2:1]([O:3][C:4](=[O:22])[CH2:5][CH:6]1[CH2:11][CH2:10][N:9]([C:12]([O:14][CH2:15][C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)=[O:13])[CH2:8][CH2:7]1)[CH3:2].C[Si](C)(C)[N-][Si](C)(C)C.[Li+].[CH2:33](Br)[CH:34]=[CH2:35]>O1CCCC1>[CH2:1]([O:3][C:4]([CH:5]([CH:6]1[CH2:11][CH2:10][N:9]([C:12]([O:14][CH2:15][C:16]2[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=2)=[O:13])[CH2:8][CH2:7]1)[CH2:35][CH:34]=[CH2:33])=[O:22])[CH3:2]

Participants

Conditions

Temperature: 25 °C

Procedure

To a −78° C. solution of benzyl 4-(2-ethoxy-2-oxoethyl)piperidine-1-carboxylate (5.02 g, 16.4 mmol) in tetrahydrofuran (90 mL) was added lithium hexamethyldisilazide (1.0 M in THF, 18.1 mL, 18.1 mmol). After 1 h, allyl bromide (2.19 g, 18.1 mmol) was added, the reaction stirred at this temperature for 0.5 h, then warmed to 25° C. After 3 h, the reaction was quenched with saturated aqueous ammonium chloride and extracted with ethyl acetate (2×). The combined organic extracts were dried over magnesium sulfate, filtered, and concentrated. Purification by silica gel chromatography (100% hexanes→40% hexanes/ethyl acetate) to give the title compound (4.08 g). MS 346.1 (M+1).

Workup

waitAfter 3 h
customthe reaction was quenched with saturated aqueous ammonium chloride
extractionextracted with ethyl acetate (2×)
dry with materialThe combined organic extracts were dried over magnesium sulfate
filtrationfiltered
concentrationconcentrated
customPurification by silica gel chromatography (100% hexanes→40% hexanes/ethyl acetate)

Sources & evidence

ORD record: ord-22fa2822697e46c3864e8ce2c86f0b19
Source dataset: uspto-grants-2011_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08039460B2

Reaction notes

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