Tetrahydrofuran → (3aS-cis)-(-)-3,3a,8,8a-Tetrahydro-2H-indeno[1,2-d]oxazol-2-one
Reaction equation
[NH2:1][C@H:2]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH2:4][C@H:3]1[OH:11].[OH-].[K+].C1C[O:17][CH2:16]C1.C(=O)(OC(Cl)(Cl)Cl)OC(Cl)(Cl)Cl>O.CCOC(C)=O>[O:11]1[C@@H:3]2[CH2:4][C:5]3[CH:6]=[CH:7][CH:8]=[CH:9][C:10]=3[C@@H:2]2[NH:1][C:16]1=[O:17]Participants
7
Reactant 4
Product 1
Reagents, catalysts & solvents 2
Conditions
- Temperature
- 0 °C
Procedure
To a solution of (1S,2R)-1-amino-2,3-dihydro-1H-inden-2-ol (500 mg, 3.35 mmol) in water (20 mL) at 0° C. was added potassium hydroxide (1128 mg, 20.1 mmol) followed by THF (20 mL) and the reaction was stirred at 0° C. for 20 minutes. Bis(trichloromethyl) carbonate (995 mg, 3.35 mmol) was added and the reaction was stirred at 0° C. for 2 hours. The reaction was poured into EtOAc and the organic phase washed with 1N HCl, 1N NaOH and brine. After drying over MgSO4, concentration yielded (3aS,8aR)-3,3a,8,8a-tetrahydro-2H-indeno[1,2-d]oxazol-2-one (574 mg, 97.8% yield) as a white solid.
Workup
- stirringthe reaction was stirred at 0° C. for 2 hours
- washthe organic phase washed with 1N HCl, 1N NaOH and brine
- dry with materialAfter drying over MgSO4, concentration
Sources & evidence
- ORD record
- ord-9bc86bd6a1da4397818b163984eeba32
- Source dataset
- uspto-grants-2014_10
- Patent number
- US08865726B2
Reaction notes
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