Methanol → cis-3-(allyloxy)-6-methoxy-2,3-dihydro-1H-inden-1-amine

HRID 1391709Notes

Reaction equation

HRID 1391709 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

5

Reactant 3

HCID 887MethanolHCID 11430Potassium CarbonateHCID 86610861cis-N-(3-(Allyloxy)-6-methoxy-2,3-dihydro-1H-inden-1-yl)-2,2,2-trifluoroacetamide

Product 1

HCID 69314472cis-3-(allyloxy)-6-methoxy-2,3-dihydro-1H-inden-1-amineYield 99.6%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Step C (3): cis-N-(3-(Allyloxy)-6-methoxy-2,3-dihydro-1H-inden-1-yl)-2,2,2-trifluoroacetamide (650 mg, 2.06 mmol) from stepC (2), potassium carbonate (1.42 g, 10.3 mmol) and MeOH (70 mL)/H2O (4.4 mL) were heated at reflux for 7 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 in vacuo to afford 450 mg (99% yield) of cis-3-(allyloxy)-6-methoxy-2,3-dihydro-1H-inden-1-amine as a light brown oil: LC-MS (M+H)+=220.2; 1H NMR (500 MHz, DMSO-d6) δ 7.19 (d, J=8.24 Hz, 1H), 6.97 (d, J=2.14 Hz, 1H), 6.78 (dd, J=8.24, 2.44 Hz, 1H), 5.81-6.07 (m, 1H), 5.30 (dd, J=17.09, 1.83 Hz, 1H), 5.15 (dd, J=10.53, 1.68 Hz, 1H), 4.72 (t, J=6.87 Hz, 1H), 4.02-4.21 (m, 2H), 3.96 (t, J=7.48 Hz, 1H), 3.73 (s, 3H), 2.64-2.88 (m, 1H), 1.39-1.58 (m, 1H).

Workup

  1. temperatureat reflux for 7 h
  2. concentrationThe reaction mixture was concentrated in vacuo
  3. extractionAdded water to the residue, extracted with EtOAc
  4. washwashed the organic layers with brine
  5. dry with materialdried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-8226e2e2e061456fa7445250dfea0d7c
Source dataset
uspto-grants-2008_03
Patent number
US07338974B2

Reaction notes

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