6-AMINO-2-N-BOC-1,2,3,4-TETRAHYDRO-ISOQUINOLINE Chemical Properties

Boiling point:

394.7±42.0 °C(Predicted)

Density 

1.145±0.06 g/cm3(Predicted)

storage temp. 

2-8°C(protect from light)

pka

4.35±0.20(Predicted)

Appearance

Off-white to yellow Solid

InChI

InChI=1S/C14H20N2O2/c1-14(2,3)18-13(17)16-7-6-10-8-12(15)5-4-11(10)9-16/h4-5,8H,6-7,9,15H2,1-3H3

InChIKey

OLOIFCYZWOTWRO-UHFFFAOYSA-N

SMILES

C1C2=C(C=C(N)C=C2)CCN1C(OC(C)(C)C)=O

CAS DataBase Reference

164148-92-9(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xn,N

Risk Statements 

36/37/38-50-22

Safety Statements 

26-36/37/39-61

RIDADR 

UN2811

HS Code 

2922390090

6-AMINO-2-N-BOC-1,2,3,4-TETRAHYDRO-ISOQUINOLINE Usage And Synthesis

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

6-AMINO-2-N-BOC-1,2,3,4-TETRAHYDRO-ISOQUINOLINE(164148-92-9)Related Product Information

• N-CARBAMYL-L-GLUTAMIC ACID
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• 5,6,7,8-TETRAHYDROISOQUINOLINE
• 1,2,3,4-TETRAHYDROISOQUINOLINE
• T-BUTYL 4-BROMOBUTYRATE
• [2-(3-AMINO-PHENYL)-ETHYL]-CARBAMIC ACID TERT-BUTYL ESTER
• 6-AMINO-2-N-BOC-1,2,3,4-TETRAHYDRO-ISOQUINOLINE
• 6-AMINO-1,2,3,4-TETRAHYDRO-ISOQUINOLINE
• tert-butyl 6-[(methylsulfonyl)amino]-3,4-dihydroisoquinoline-2(1H)-carboxylate