Benzyl chloroformate → Benzyl [1-(benzyloxy)but-3-en-2-yl]carbamate

HRID 595328Notes

Reaction equation

HRID 595328 reaction equation
[C:1](Cl)(=[O:10])[O:2][CH2:3][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.Cl.[CH2:13]([O:20][CH2:21][CH:22]([NH2:25])[CH:23]=[CH2:24])[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1.CCN(C(C)C)C(C)C>C(#N)C.O>[CH2:13]([O:20][CH2:21][CH:22]([NH:25][C:1](=[O:10])[O:2][CH2:3][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1)[CH:23]=[CH2:24])[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1

Participants

6

Reactant 3

HCID 10387Benzyl chloroformateHCID 81531DiisopropylethylamineHCID 135179031-(Benzyloxy)but-3-en-2-amine hydrochloride

Product 1

HCID 12180511Benzyl [1-(benzyloxy)but-3-en-2-yl]carbamate

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6342AcetonitrileSolvent

Procedure

Benzyl carbonochloridate (4.7 g, 27.4 mmol) was added dropwise over a period of 30 minutes to a mixture of 1-(benzyloxy)but-3-en-2-amine hydrochloride (3.9 g, 18 mmol) and Hunig's base (10.0 mL, 54.8 mmol) in acetonitrile (100 mL) at 0° C. The reaction mixture was stirred at room temperature for 16 hours. The reaction mixture was diluted with water and extracted with ethyl acetate. The organic layer was dried over sodium sulfate, filtered, and concentrated under reduced pressure to afford the crude product residue. The crude product residue was purified by silica gel chromatography (ethyl acetate/petroleum ether) to afford benzyl [1-(benzyloxy)but-3-en-2-yl]carbamate. MS ESI calc'd. for C19H22NO3 [M+H]+ 312. found 312. 1H NMR (300 MHz, CD3OD) δ 7.34-7.25 (m, 10H), 5.87-5.79 (m, 1H), 5.25-5.08 (m, 4H), 4.51 (s, 2H), 4.38-4.36 (m, 1H), 3.54-3.44 (m, 2H).

Workup

  1. extractionextracted with ethyl acetate
  2. dry with materialThe organic layer was dried over sodium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated under reduced pressure
  5. customto afford the crude product residue
  6. customThe crude product residue was purified by silica gel chromatography (ethyl acetate/petroleum ether)

Sources & evidence

ORD record
ord-585cc6f1134e40a286e8ebe8eed9deed
Source dataset
uspto-grants-2016_01
Patent number
US09242984B2

Reaction notes

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