Benzyl Alcohol → Benzyl (3-oxocyclobutyl)carbamate
Reaction equation
[O:1]=[C:2]1[CH2:5][CH:4](C(O)=O)[CH2:3]1.C1[CH2:13][O:12]CC1.C1(C)C=CC=CC=1.C1(P([N:35]=[N+]=[N-])(C2C=CC=CC=2)=O)C=CC=CC=1.[CH2:38]([OH:45])[C:39]1[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=1>C(OC(=O)C)C>[CH2:38]([O:45][C:13](=[O:12])[NH:35][CH:4]1[CH2:3][C:2](=[O:1])[CH2:5]1)[C:39]1[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=1Participants
Conditions
- Temperature
- 60 °C
Procedure
A solution of (3-oxo-cyclobutyl)-carboxylic acid (506 mg, 4.4 mmol) and Et3N(734 μl) in 1:1 THF-Toluene (15 mL) was treated with diphenyl phosphoryl azide (956 μL, 4.4 mmol). The solutions warmed to 60° C. over ca. 45 minutes, at which point nitrogen evolution was noted. After 3 hours, benzyl alcohol (500 μL, 4.8 mmol) was added and the solution was kept at 60° C. for 4 hours. After cooling to room temperature, the solution was diluted with ethylacetate, was washed with saturated aqueous sodium bicarbonate (1 time), 0.5NHCl (2 times) NaHCO3 (1 time), was dried (MgSO4), filtered, and was purified by silica gel chromatography (4:1 Hexanes-Ethylacetate) to afford 405 mg of the title compound. 1HNMR(400 MHz, CDCl3) 7.32 (m,5H), 5.44 (s,1H), 5.08(s,2H) 4.29(m,1H), 3.36(m, 2H), 3.06 (m, 2H). LRMS (APCl−) 218.1 (M−H)−.
Workup
- waitthe solution was kept at 60° C. for 4 hours
- temperatureAfter cooling to room temperature
- washwas washed with saturated aqueous sodium bicarbonate (1 time), 0.5NHCl (2 times) NaHCO3 (1 time)
- dry with materialwas dried (MgSO4)
- filtrationfiltered
- customwas purified by silica gel chromatography (4:1 Hexanes-Ethylacetate)
Sources & evidence
- ORD record
- ord-edd9656f91a6412a91b9e4aa789cf9eb
- Source dataset
- uspto-grants-2004_04
- Patent number
- US06720427B2
Reaction notes
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