2,3-Dibromopropene → Benzyl 4-[3-bromo-1-(ethoxycarbonyl)but-3-en-1-yl]piperidine-1-carboxylate

HRID 1664789Notes

Reaction equation

HRID 1664789 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].[Br:23][C:24]([CH2:26]Br)=[CH2:25]>O1CCCC1>[Br:23][C:24](=[CH2:25])[CH2:26][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)[C:4]([O:3][CH2:1][CH3:2])=[O:22]

Participants

4

Reactant 2

HCID 105522,3-DibromopropeneHCID 12902702Benzyl 4-(2-ethoxy-2-oxoethyl)piperidine-1-carboxylate

Product 1

HCID 86620119Benzyl 4-[3-bromo-1-(ethoxycarbonyl)but-3-en-1-yl]piperidine-1-carboxylateYield 21.7%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Lithium hexamethyldisilylazide (1.0 M in THF; 7.20 mL, 7.20 mmol) was added to solution of benzyl 4-(2-ethoxy-2-oxoethyl)piperidine-1-carboxylate (2.0 g, 6.55 mmol) in tetrahydrofuran (30 mL) at −78° C. After 40 min, 2,3-dibromoprop-1-ene (0.70 mL, 7.20 mmol) was added. After 2 h, the reaction mixture was warmed to ambient temperature. After 18 h, the mixture was quenched with saturated 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 (80% hexanes/ethyl acetate→40% hexanes/ethyl acetate) gave the title compound (603 mg). MS 424.0 (M).

Workup

  1. waitAfter 2 h
  2. waitAfter 18 h
  3. customthe mixture was quenched with saturated ammonium chloride
  4. extractionextracted with ethyl acetate (2×)
  5. dry with materialThe combined organic extracts were dried over magnesium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customPurification by silica gel chromatography (80% hexanes/ethyl acetate→40% hexanes/ethyl acetate)

Sources & evidence

ORD record
ord-0df9f953a44a4cb7872fd23fd0f2dcd3
Source dataset
uspto-grants-2011_10
Patent number
US08039460B2

Reaction notes

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