Hydrazine → rac-(1R,2R)-2-methoxy-2,3-dihydro-1H-inden-1-amine

To a mixture of 2-[(1R,2R)-2-methoxy-2,3-dihydro-1H-inden-1-yl]-1H-isoindole-1,3(2H)-dione (4.13 g, 0.00141 mol) in ethanol (3.38 mL) under an atmosphere of argon was added hydrazine (0.0442 mL, 0.0580 mol). The reaction mixture was allowed to stir at rt overnight. White solid byproduct crashed out of solution. TLC showed no starting material. The reaction mixture was concentrated, and the residue was suspended in DCM and filtered. The filtrate was concentrated in vacuo. 1H NMR showed that the reaction had not gone to completion. The yellow oil was therefore stirred at reflux for 3 h. LCMS confirmed reaction was complete. The reaction mixture was cooled to rt, concentrated in vacuo, triturated with DCM, filtered, and the filtrate was concentrated in vacuo to give product as a yellow oil (0.154 g, 64%). LC/MS: Rt=0.68 min, ES+ 164 (AA standard).

1. concentrationThe reaction mixture was concentrated
2. filtrationfiltered
3. concentrationThe filtrate was concentrated in vacuo
4. stirringThe yellow oil was therefore stirred
5. temperatureat reflux for 3 h
6. customreaction
7. temperatureThe reaction mixture was cooled to rt
8. concentrationconcentrated in vacuo
9. customtriturated with DCM
10. filtrationfiltered
11. concentrationthe filtrate was concentrated in vacuo

ORD record

ord-f67904c9bf2a49bb8209904c582c38e1

Source dataset

uspto-grants-2012_06

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08207177B2