Ammonia → (R)-2-amino-1-((S)-2,5-dihydrofuran-2-yl)ethanol
Reaction equation
[OH:1][CH2:2][CH2:3]NC(=O)[O-].[NH3:8].[CH3:9][CH:10]([OH:12])[CH3:11].[CH3:13]O>[OH-].[NH4+]>[NH2:8][CH2:9][C@H:10]([C@@H:11]1[CH:13]=[CH:3][CH2:2][O:1]1)[OH:12]Participants
6
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 75 °C
Procedure
Alternative preparation of Benzyl (R)-2-(S)-2,5-dihydrofuran-2-yl)-2-hydroxyethylcarbamate (18). Alcohol (14) (4.3 g, 15.1 mmol) was dissolved in ammonium hydroxide (30 mL) and a solution of ammonia in 2-propanol (20 mL, 2.0M, 80 mmol). The solution was divided into two equal portions then heated at 75° C. in sealed tubes for 16 hours. The mixtures were combined using methanol then the solvents were removed in vacuo. The residue was azeotroped with diethyl ether (3×20 mL) to obtain (R)-2-amino-1-((S)-2,5-dihydrofuran-2-yl)ethanol which was used without further purification.
Workup
- customthe solvents were removed in vacuo
- customThe residue was azeotroped with diethyl ether (3×20 mL)
Sources & evidence
- ORD record
- ord-4f4f4c97eb624fb38ce476c10c5d8e61
- Source dataset
- uspto-grants-2011_10
- Patent number
- US08039641B2
Reaction notes
Loading…