Acetic Acid → 6,8-Dichloro-2-propyl-2,3,3a,4,5,9b-hexahydro-1H-benzo[e]isoindol-7-yl-amine
Reaction equation
[Cl:1][C:2]1[C:14]2[CH2:13][CH2:12][CH:11]3[CH:7]([CH2:8][NH:9][CH2:10]3)[C:6]=2[CH:5]=[C:4]([Cl:15])[C:3]=1[NH2:16].[CH:17](=O)[CH2:18][CH3:19].C(O)(=O)C.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>O1CCCC1>[Cl:1][C:2]1[C:14]2[CH2:13][CH2:12][CH:11]3[CH:7]([CH2:8][N:9]([CH2:17][CH2:18][CH3:19])[CH2:10]3)[C:6]=2[CH:5]=[C:4]([Cl:15])[C:3]=1[NH2:16]Participants
6
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Procedure
6,8-Dichloro-2,3,3a,4,5,9b-hexahydro-1H-benzo[e]isoindol-7-ylamine (275 mg, 1.07 mmol) and propionaldehyde (81 μl, 1.12 mmol) were dissolved in tetrahydrofuran (25 ml). Acetic acid (90 μl, 1.6 mmol) and sodium trisacetoxyborohydride (340 mg, 1.6 mmol) were sequentially added to the reaction mixture and stirred for 1 hour at room temperature. The reaction mixture was concentrated and the residue was dissolved in a 1 M NaOH solution (20 ml) and ethyl acetate (20 ml). The aqueous phase was extracted once more with ethyl acetate. The combined organic phases were dried over magnesium sulfate, filtered, and evaporated to dryness to yield the pure product (295 mg, 92%).
Workup
- concentrationThe reaction mixture was concentrated
- dissolutionthe residue was dissolved in a 1 M NaOH solution (20 ml) and ethyl acetate (20 ml)
- extractionThe aqueous phase was extracted once more with ethyl acetate
- dry with materialThe combined organic phases were dried over magnesium sulfate
- filtrationfiltered
- customevaporated to dryness
Sources & evidence
- ORD record
- ord-adfeb5960ebb41d79cfb215631baa8b3
- Source dataset
- uspto-grants-2013_07
- Patent number
- US08486984B2
Reaction notes
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