L-Tryptophan → L-(-)-Tryptophanol
Reaction equation
[NH2:1][C@H:2]([C:13](O)=[O:14])[CH2:3][C:4]1[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[NH:6][CH:5]=1>CO[2H]>[NH2:1][C@@H:2]([CH2:3][C:4]1[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[NH:6][CH:5]=1)[CH2:13][OH:14]Participants
3
Reactant 1
Product 1
Reagents, catalysts & solvents 1
Procedure
The title compound was prepared from (S)-tryptophan according to Method D and was isolated as a solid in 92% yield. δH (MeOD-d3) 7.46 (1H, d, J 7.9 Hz), 7.21 (1H, d, J 8.0 Hz), 6.96 (3H, m), 3.79 (1H, dd, J 11.3 and 3.6 Hz), 3.54 (1H, dd, J 11.3 and 6.2 Hz), 3.05 (1H, m), 2.80 (1H, m), 2.61 (1H, m). Note: exchangeable protons not evident in MeOD.
Workup
- customwas isolated as a solid in 92% yield
Sources & evidence
- ORD record
- ord-007bb295874144248d771a25b8014a86
- Source dataset
- uspto-grants-2011_02
- Patent number
- US07888344B2
Reaction notes
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