Methanol → (1S,3R)-3-(allyloxy)-6-methoxy-2,3-dihydro-1H-inden-1-amine
Reaction equation
[CH2:1]([O:4][C@H:5]1[C:13]2[C:8](=[CH:9][C:10]([O:14][CH3:15])=[CH:11][CH:12]=2)[C@@H:7]([NH:16]C(=O)C(F)(F)F)[CH2:6]1)[CH:2]=[CH2:3].C(=O)([O-])[O-].[K+].[K+].CO>O>[CH2:1]([O:4][C@H:5]1[C:13]2[C:8](=[CH:9][C:10]([O:14][CH3:15])=[CH:11][CH:12]=2)[C@@H:7]([NH2:16])[CH2:6]1)[CH:2]=[CH2:3]Participants
Procedure
Step U (2): N-((1S,3R)-3-(allyloxy)-6-methoxy-2,3-dihydro-1H-inden-1-yl)-2,2,2-trifluoroacetamide (1.28 g, 4.06 mmol) from Step U (1), potassium carbonate (2.85 g, 20.8 mmol) and MeOH (92 mL)/H2O (6 mL) were heated at reflux for 16 h. The reaction mixture was concentrated in vacuo. Added water to the residue, extracted with EtOAc, washed the organic layers with brine, dried over Na2SO4, filtered and concentrated to afford 780 mg (quantitative yield) of the title compound as light brown oil. HRMS (M+H)+=220.1336; [α]D +18.72 (c=8.86 mg/mL, ethanol) 1H NMR (500 MHz, CDCl3) δ ppm 1.66 (s, 1H) 1.76 (d, J=12.82 Hz, 1H) 2.74-2.83 (m, 1H) 3.81 (s, 3H) 4.04-4.18 (m, 3H) 4.77 (t, J=5.80 Hz, 1H) 5.18 (dd, J=10.38, 1.53 Hz, 1H) 5.32 (dd, J=17.24, 1.68 Hz, 1H) 5.97 (dd, 1H) 6.90 (d, J=2.44 Hz, 1H) 7.30 (d, J=8.24 Hz, 1H).
Workup
- temperatureat reflux for 16 h
- concentrationThe reaction mixture was concentrated in vacuo
- extractionAdded water to the residue, extracted with EtOAc
- washwashed the organic layers with brine
- dry with materialdried over Na2SO4
- filtrationfiltered
- concentrationconcentrated
Sources & evidence
- ORD record
- ord-7301532b375c4c9b9e84d7d4167f0db7
- Source dataset
- uspto-grants-2010_08
- Patent number
- US07772221B2
Reaction notes
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