Benzyl allyl(2-methylallyl)carbamate → benzyl 3-methyl-2,5-dihydro-1H-pyrrole-1-carboxylate

HRID 877828Notes

Reaction equation

HRID 877828 reaction equation
[CH2:1]([N:4]([CH2:15][C:16]([CH3:18])=[CH2:17])[C:5](=[O:14])[O:6][CH2:7][C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)C=C>ClCCl.Cl[Ru](=CC1C=CC=CC=1)([P](C1CCCCC1)(C1CCCCC1)C1CCCCC1)([P](C1CCCCC1)(C1CCCCC1)C1CCCCC1)Cl>[CH3:18][C:16]1[CH2:15][N:4]([C:5]([O:6][CH2:7][C:8]2[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=2)=[O:14])[CH2:1][CH:17]=1

Participants

4

Reactant 1

HCID 68291606Benzyl allyl(2-methylallyl)carbamate

Product 1

HCID 20090036benzyl 3-methyl-2,5-dihydro-1H-pyrrole-1-carboxylateYield 91%

Reagents, catalysts & solvents 2

HCID 178479819HCID 178479819, compoundCatalystHCID 6344DichloromethaneSolvent

Procedure

A solution of benzyl allyl(2-methylallyl)carbamate (20.2 g, 82 mmol) in dichloromethane (500 mL) was purged with argon for 5 min. Grubbs I catalyst (1.694 g, 2.059 mmol) was added and the resulting purple solution was warmed to a gentle reflux under argon for 24 h. The mixture was concentrated and purified by silica gel chromatography, eluting with 0-20% ethyl acetate in hexanes, to give benzyl 3-methyl-2,5-dihydro-1H-pyrrole-1-carboxylate (16.2 g, 91% yield). 1H NMR (400 MHz, chloroform-d) δ ppm 7.65-7.28 (m, 5H), 5.69-5.27 (m, 2H), 4.30-3.91 (m, 5H), 1.84-1.68 (m, 3H); MS (ES+) m/z: 218.2 (M+H).

Workup

  1. temperaturethe resulting purple solution was warmed to
  2. temperaturea gentle reflux under argon for 24 h
  3. concentrationThe mixture was concentrated
  4. custompurified by silica gel chromatography
  5. washeluting with 0-20% ethyl acetate in hexanes

Sources & evidence

ORD record
ord-376a297b01c34805b31ab03adcb8414f
Source dataset
uspto-grants-2015_03
Patent number
US08987268B2

Reaction notes

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