1,8-Diazabicyclo(5.4.0)undec-7-ene → Tert-butyl 4-methylpent-3-enyloxycarbamate

HRID 1917495Notes

Reaction equation

HRID 1917495 reaction equation
Br[CH2:2][CH2:3][CH:4]=[C:5]([CH3:7])[CH3:6].[OH:8][NH:9][C:10](=[O:16])[O:11][C:12]([CH3:15])([CH3:14])[CH3:13].C1CCN2C(=NCCC2)CC1>CC#N>[CH3:6][C:5]([CH3:7])=[CH:4][CH2:3][CH2:2][O:8][NH:9][C:10](=[O:16])[O:11][C:12]([CH3:15])([CH3:14])[CH3:13]

Participants

5

Reactant 3

HCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 97534tert-butyl N-hydroxycarbamateHCID 1375215-Bromo-2-methyl-2-pentene

Product 1

HCID 57999201Tert-butyl 4-methylpent-3-enyloxycarbamateYield 70%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a solution of 5-bromo-2-methylpent-2-ene (1.33 mL, 10.0 mmol) in CH3CN (25 mL) was added tert-butyl hydroxycarbamate (2.0 g, 15.0 mmol) and DBU (4.5 mL, 30 mmol) at 0° C. and the reaction mixture stirred at r.t. for overnight. Quenched with saturated NH4Cl solution and extracted with brine. Combined organic layers washed with brine and dried over anhydrous Na2SO4, filtered and concentrated to provide yellow oil, which was purified by flash chromatography (50% EtOAc-hexane) to yield tert-butyl 4-methylpent-3-enyloxycarbamate (750 mg, 70%) as a viscous oil. 1H NMR (400 MHz, CHLOROFORM-d) δ ppm 1.40 (s, 9H) 1.54 (s., 3H) 1.61 (s., 3H) 2.21-2.31 (m, 2H) 3.70-3.78 (m, 2H) 5.02-5.10 (m, 1H). MS (ES) [M+H] calculated for C11H22NO3, 216.15; found 216.10.

Workup

  1. customQuenched with saturated NH4Cl solution
  2. extractionextracted with brine
  3. washCombined organic layers washed with brine
  4. dry with materialdried over anhydrous Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customto provide yellow oil, which
  8. customwas purified by flash chromatography (50% EtOAc-hexane)

Sources & evidence

ORD record
ord-8b6d2b9bf56a4f078b3d98c460a6fbe8
Source dataset
uspto-grants-2013_12
Patent number
US08618290B2

Reaction notes

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