(3-bromoprop-1-en-2-yl)benzene → HCID 67440613, compound

HRID 1664784Notes

Reaction equation

HRID 1664784 reaction equation
[CH3:1][O:2][C:3](=[O:21])[CH2:4][CH:5]1[CH2:10][CH2:9][N:8]([C:11]([O:13][CH2:14][C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)=[O:12])[CH2:7][CH2:6]1.Br[CH2:23][C:24]([C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1)=[CH2:25]>O1CCCC1>[CH3:1][O:2][C:3]([CH:4]([CH:5]1[CH2:6][CH2:7][N:8]([C:11]([O:13][CH2:14][C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)=[O:12])[CH2:9][CH2:10]1)[CH2:25][C:24]([C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1)=[CH2:23])=[O:21]

Participants

4

Reactant 2

HCID 234998(3-bromoprop-1-en-2-yl)benzeneHCID 40429392Benzyl 4-(2-methoxy-2-oxoethyl)piperidine-1-carboxylate

Product 1

HCID 67440613HCID 67440613, compoundYield 77.9%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Lithium hexamethyldisilylazide (1.0 M in THF; 7.31 mL, 7.31 mmol) was added to solution of benzyl 4-(2-methoxy-2-oxoethyl)piperidine-1-carboxylate (1.94 g, 6.65 mmol) in tetrahydrofuran (35 mL) at −78° C. After 40 min, [1-(bromomethyl)vinyl]benzene (1.08 mL, 7.31 mmol) was added and the reaction mixture was warmed to ambient temperature. After 18 h, the mixture 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) gave the title compound (2.11 g). MS 408.2 (M+1).

Workup

  1. waitAfter 18 h
  2. customthe mixture was quenched with saturated aqueous ammonium chloride
  3. extractionextracted with ethyl acetate (2×)
  4. dry with materialThe combined organic extracts were dried over magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customPurification by silica gel chromatography (100% hexanes→40% hexanes/ethyl acetate)

Sources & evidence

ORD record
ord-6c8b49e2620d4dc5809317fc8a456a3e
Source dataset
uspto-grants-2011_10
Patent number
US08039460B2

Reaction notes

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