(S)-1-((S)-2,5-Dihydrofuran-2-yl)-2-hydroxyethyl 4-methylbenzenesulfonate → (R)-2-amino-1-((S)-2,5-dihydrofuran-2-yl)ethanol
Reaction equation
[O:1]1[CH2:5][CH:4]=[CH:3][C@H:2]1[C@H:6]([OH:19])[CH2:7][NH:8]C(=O)OCC1C=CC=CC=1.CC1C=CC(S(O[C@H]([C@@H]2C=CCO2)CO)(=O)=O)=CC=1>[OH-].[NH4+]>[NH2:8][CH2:7][C@H:6]([C@@H:2]1[CH:3]=[CH:4][CH2:5][O:1]1)[OH:19]Participants
4
Conditions
- Temperature
- 75 °C
Procedure
Alternative preparation of Benzyl (R)-2-((S)-2,5-dihydrofuran-2-yl)-2-hydroxyethylcarbamate (18); ‘One-pot’ procedure 3; Aqueous Conditions. (S)-1-((S)-2,5-Dihydrofuran-2-yl)-2-hydroxyethyl 4-methylbenzenesulfonate (14) (0.95 g, 3.35 mmol) was suspended in ammonium hydroxide (4 mL) then stirred and heated at 75° C. in a sealed tube for 6 hours during which time the two liquid phases became a single phase solution. The mixture was stirred at ambient temperature for 20 hours then the solvents were removed in vacuo. The residue was azeotroped with diethyl ether (3×10 mL) to obtain (R)-2-amino-1-((S)-2,5-dihydrofuran-2-yl)ethanol which was used without further purification.
Workup
- stirringThe mixture was stirred at ambient temperature for 20 hours
- customthe solvents were removed in vacuo
- customThe residue was azeotroped with diethyl ether (3×10 mL)
Sources & evidence
- ORD record
- ord-19f04da2409e42609b57f89a16cce3f0
- Source dataset
- uspto-grants-2011_10
- Patent number
- US08039641B2
Reaction notes
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