3-Bromo-2-methyl-1-propene → HCID 67440198, compound

HRID 1664778Notes

Reaction equation

HRID 1664778 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[CH2:24][C:25]([CH3:27])=[CH2:26]>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)[CH2:26][C:25]([CH3:27])=[CH2:24])=[O:22])[CH3:2]

Participants

4

Reactant 2

HCID 3577853-Bromo-2-methyl-1-propeneHCID 12902702Benzyl 4-(2-ethoxy-2-oxoethyl)piperidine-1-carboxylate

Product 1

HCID 67440198HCID 67440198, compoundYield 48.9%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Lithium hexamethyldisilylazide (1.0 M in THF; 18.0 mL, 18.0 mmol) was added to a solution of benzyl 4-(2-ethoxy-2-oxoethyl)piperidine-1-carboxylate (5.0 g, 16.4 mmol) in tetrahydrofuran (90 mL) at −78° C. After 40 min, 3-bromo-2-methylprop-1-ene (1.81 mL, 18.0 mmol) was added and the reaction mixture was allowed to warm to ambient temperature. After 16 h, the reaction was quenched by the addition of saturated aqueous ammonium chloride and extracted with ethyl acetate (2×). The combined organic layers were dried over magnesium sulfate, filtered, and concentrated. Purified by silica gel chromatography (100% hexanes→40% hexanes/ethyl acetate) to give the title compound (2.88 g). MS 360.2 (M+1).

Workup

  1. waitAfter 16 h
  2. customthe reaction was quenched by the addition of saturated aqueous ammonium chloride
  3. extractionextracted with ethyl acetate (2×)
  4. dry with materialThe combined organic layers were dried over magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customPurified by silica gel chromatography (100% hexanes→40% hexanes/ethyl acetate)

Sources & evidence

ORD record
ord-22870e6c9e6042f881513e3f2d96bf4a
Source dataset
uspto-grants-2011_10
Patent number
US08039460B2

Reaction notes

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