N-Boc-endo-3-aminotropane

N-Boc-endo-3-aminotropane Property

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

HS Code 

2924297099

Hazard and Precautionary Statements (GHS)

Symbol(GHS)

Signal word

Danger

Hazard statements

H302Harmful if swallowed

H315Causes skin irritation

H318Causes serious eye damage

H335May cause respiratory irritation

Precautionary statements

P264Wash hands thoroughly after handling.

P264Wash skin thouroughly after handling.

P270Do not eat, drink or smoke when using this product.

P280Wear protective gloves/protective clothing/eye protection/face protection.

P301+P312IF SWALLOWED: call a POISON CENTER or doctor/physician IF you feel unwell.

P302+P352IF ON SKIN: wash with plenty of soap and water.

P305+P351+P338IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.

P310Immediately call a POISON CENTER or doctor/physician.

P321Specific treatment (see … on this label).

P330Rinse mouth.

P332+P313IF SKIN irritation occurs: Get medical advice/attention.

P362Take off contaminated clothing and wash before reuse.

P501Dispose of contents/container to..…

N-Boc-endo-3-aminotropane Chemical Properties,Usage,Production

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