Benzyl Alcohol → 2-Oxa-5-azaspiro[3.4]octane-5-carboxylic acid, 7-[[(phenylmethoxy)carbonyl]amino]-, 1,1-dimethylethyl ester
Reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:15][CH:14](C(O)=O)[CH2:13][C:9]21[CH2:12][O:11][CH2:10]2)=[O:7])([CH3:4])([CH3:3])[CH3:2].P(N=[N+]=[N-])(=O)([O:27][C:28]1C=CC=CC=1)OC1C=CC=CC=1.CC[N:40](CC)CC.[C:45]1([CH2:51][OH:52])[CH:50]=[CH:49][CH:48]=[CH:47][CH:46]=1>C1(C)C=CC=CC=1>[CH2:51]([O:52][C:28]([NH:40][CH:14]1[CH2:13][C:9]2([CH2:10][O:11][CH2:12]2)[N:8]([C:6]([O:5][C:1]([CH3:2])([CH3:3])[CH3:4])=[O:7])[CH2:15]1)=[O:27])[C:45]1[CH:50]=[CH:49][CH:48]=[CH:47][CH:46]=1Participants
6
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 80 °C
Procedure
To a solution of 5-(tert-butoxycarbonyl)-2-oxa-5-azaspiro[3.4]octane-7-carboxylic acid (444 mg, 1.72 mmol) in 5 mL of anhydrous toluene was added diphenyl phosphorazidate (407 μL, 1.89 mmol) and NEt3 (275 μL, 1.89 mmol). The mixture was heated at 80° C. for 3 hours. Then to the mixture was added phenylmethanol (0.5 mL). The resulting mixture was then heated at 90° C. overnight. The reaction mixture was concentrated in vacuo. The residue was purified by flash column (eluting with 0-30% EtOAc in PE) to afford tert-butyl 7-{[(benzyloxy)carbonyl]amino}-2-oxa-5-azaspiro[3.4]octane-5-carboxylate (577 mg, yield: 92.6%) as light viscous oil.
Workup
- temperatureThe resulting mixture was then heated at 90° C. overnight
- concentrationThe reaction mixture was concentrated in vacuo
- customThe residue was purified by flash column (eluting with 0-30% EtOAc in PE)
Sources & evidence
- ORD record
- ord-fedfe94b34c74e018cb50e5e698c0179
- Source dataset
- uspto-grants-2015_12
- Patent number
- US09206191B2
Reaction notes
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