6-Amino-2-N-Boc-1,2,3,4-tetrahydro-isoquinoline

Uses

6-Amino-2-N-Boc-1,2,3,4-tetrahydroisoquinoline is used as a reagent in the preparation of potent and long acting oral factor Xa inhibitors.

Synthesis

General procedure for the synthesis of 6-amino-2-N-BOC-1,2,3,4-tetrahydro-isoquinoline from compound (CAS:1154424-63-1): ammonium formate (3.68 g, 57.5 mmol) was added to a stirred ethanol (EtOH, 25 mL) solution of compound 2 (2.2 g, 5.75 mmol) and the reaction mixture was heated to refluxed for 6 hours. Upon completion of the reaction, the mixture was cooled to room temperature and filtered through a diatomaceous earth bed to remove insoluble impurities. Subsequently, the diatomaceous earth bed and the filtrate were combined and concentrated under reduced pressure to afford compound 3 (1.3 g, 91% yield) as a dark brown oil, which could be used in subsequent reactions without further purification.

References

[1] Patent: WO2009/158571, 2009, A1. Location in patent: Page/Page column 165; 167; 168