tert-Butanol → tert-Butyl ((3-(3-bromophenyl)oxetan-3-yl)methyl)carbamate
Reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([C:8]2([CH2:12]C(O)=O)[CH2:11][O:10][CH2:9]2)[CH:5]=[CH:6][CH:7]=1.C([N:18]([CH2:21]C)CC)C.C1(P(N=[N+]=[N-])(C2C=CC=CC=2)=[O:30])C=CC=CC=1.[C:40]([OH:44])([CH3:43])([CH3:42])[CH3:41]>>[Br:1][C:2]1[CH:3]=[C:4]([C:8]2([CH2:12][NH:18][C:21](=[O:30])[O:44][C:40]([CH3:43])([CH3:42])[CH3:41])[CH2:9][O:10][CH2:11]2)[CH:5]=[CH:6][CH:7]=1Participants
Conditions
- Temperature
- 80 °C
Procedure
2-[3-(3-Bromophenyl)oxetan-3-yl]acetic acid (840 mg, 2.789 mmol) was dissolved in tert-butanol (8 mL) and triethylamine (310.5 mg, 427.7 μL, 3.068 mmol) was added followed by diphenylphosphoryl azide (844.3 mg, 661.2 μL, 3.068 mmol). Heat at 80° C. for 4 hours. The reaction was allowed to cool and the solvent removed under reduced pressure. Ethyl acetate was added and the organic layer was washed with 5% citric acid soln, NaHCO3 (sat. aq. soln.) and brine. The organics were dried over MgSO4, filtered and the solvent removed under reduced pressure. The crude product was pre-adsorbed onto silica and purified (Companion, 40 g) eluting with 2.5-50% EtOAc:Petrol ether to give tert-butyl N-[[3-(3-bromophenyl)oxetan-3-yl]methyl]carbamate as a white solid (433 mg, 45%).
Workup
- temperatureto cool
- customthe solvent removed under reduced pressure
- additionEthyl acetate was added
- washthe organic layer was washed with 5% citric acid soln
- dry with materialThe organics were dried over MgSO4
- filtrationfiltered
- customthe solvent removed under reduced pressure
- custompurified (Companion, 40 g)
- washeluting with 2.5-50% EtOAc
Sources & evidence
- ORD record
- ord-a73a310f79644aefbf02267e0ad1bf99
- Source dataset
- uspto-grants-2013_02
- Patent number
- US08367697B2
Reaction notes
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