反应详情

To a solution of 4-[(7-nitro-1,2,3,4-tetrahydro-naphthalen-2-ylamino)-methyl]-piperidine-1-carboxylic acid tert-butyl ester (485 mg, 1.25 mmol) and acetaldehyde (110 μL, 1.49 mmol) in dichloroethane (20 mL) under a nitrogen atmosphere was added sodium triacetoxyborohydride (530 mg, 2.49 mmol, 2 eq.) in a single portion. The reaction was stirred at room temperature for 24 h then concentrated in vacuo. The residue was partitioned between EtOAc (75 mL) and 5% aq. KOH (50 mL). The aqueous phase was extracted twice more with EtOAc (2×30 mL). The combined organic layers were dried over MgSO4, filtered, and concentrated onto silica (10 g). This was placed on top of a flash column and eluted with 20% acetone in hexanes. The fractions containing product were pooled and concentrated to afford 4-{[ethyl-(7-nitro-1,2,3,4-tetrahydro-naphthalen-2-yl)-amino]-methyl}-piperidine-1-carboxylic acid tert-butyl ester as a yellow oil (430 mg).

1. concentrationthen concentrated in vacuo
2. customThe residue was partitioned between EtOAc (75 mL) and 5% aq. KOH (50 mL)
3. extractionThe aqueous phase was extracted twice more with EtOAc (2×30 mL)
4. dry with materialThe combined organic layers were dried over MgSO4
5. filtrationfiltered
6. concentrationconcentrated onto silica (10 g)
7. washeluted with 20% acetone in hexanes
8. additionThe fractions containing product
9. concentrationconcentrated