N-Boc-endo-3-aminotropane Chemical Properties

Boiling point:

313.2±35.0 °C(Predicted)

Density 

1.084

storage temp. 

under inert gas (nitrogen or Argon) at 2–8 °C

pka

10.12±0.20(Predicted)

Appearance

White to off-white Solid

InChI

InChI=1/C12H22N2O2/c1-12(2,3)16-11(15)14-9-4-5-10(14)7-8(13)6-9/h8-10H,4-7,13H2,1-3H3/t9-,10-/s3

InChIKey

NZJKEPNCNBWESN-DPIMBTEZNA-N

SMILES

C(=O)(OC(C)(C)C)N1[C@H]2CC[C@H]1C[C@H](N)C2 |&1:8,11,13,r|

CAS DataBase Reference

207405-68-3

Safety Information

HS Code 

2924297099

N-Boc-endo-3-aminotropane Usage And Synthesis

Chemical Properties

White Solid

Uses

N-Boc-endo-3-aminotropane is used as a reagent in the synthesis of tropane-derived CCR5 receptor antagonists.

Synthesis

TERT-BUTYL (1R,3R,5S)-3-(BENZYLAMINO)-8-AZABICYCLO[3.2.1]OCTANE-8-CARBOXYLATE (Compound 3b, 7.0 g, 22.2 mmol) was used as a raw material, which was mixed with ammonium formate (7.0 g, 111 mmol) and 20% palladium hydroxide /carbon catalyst (0.7 g) in ethanol (200 ml). The reaction mixture was stirred at 50°C for 2 hours. After completion of the reaction, it was cooled to room temperature and the catalyst was removed by filtration. The filtrate was concentrated by rotary evaporation and purified by column chromatography to afford the target product tert-butyl endo-3-amino-8-azabicyclo[3.2.1]octane-8-carboxylate (Compound 3c, 4.7 g, 94% yield).

References

[1] Patent: US2017/44187, 2017, A1. Location in patent: Paragraph 0183; 0185
[2] Journal of Medicinal Chemistry, 2008, vol. 51, # 20, p. 6538 - 6546
[3] Patent: EP937069, 2006, B1. Location in patent: Page/Page column 74
[4] Patent: US2005/131011, 2005, A1. Location in patent: Page/Page column 18
[5] Journal of Medicinal Chemistry, 2011, vol. 54, # 11, p. 3756 - 3767

N-Boc-endo-3-aminotropane(207405-68-3)Related Product Information

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