3-Azabicyclo[3.1.0]hexane-3-carboxylicacid,6-amino-,1,1-dimethylethylester, Chemical Properties

Melting point:

45-47°

Boiling point:

275℃

Density 

1.144

Flash point:

120℃

storage temp. 

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

pka

8.52±0.20(Predicted)

Appearance

Off-white to yellow Solid

InChI

InChI=1/C10H18N2O2/c1-10(2,3)14-9(13)12-4-6-7(5-12)8(6)11/h6-8H,4-5,11H2,1-3H3/t6-,7+,8+

InChIKey

UWWZMHWHRBGMIT-JIGDXULJNA-N

SMILES

N[C@@H]1[C@@]2([H])CN(C(=O)OC(C)(C)C)C[C@@]12[H] |&1:1,2,14,r|

Safety Information

HazardClass 

IRRITANT

HS Code 

2922390090

3-Azabicyclo[3.1.0]hexane-3-carboxylicacid,6-amino-,1,1-dimethylethylester, Usage And Synthesis

Uses

(1α,5α,6α)-6-Amino-3-azabicyclo[3.1.0]hexane-3-carboxylic Acid 1,1-Dimethylethyl Ester, is an intermediate in the preparation of a novel series of Histone Deacetylase (HDAC) Inhibitors, demonstrating class I selectivity and good oral bioavailability. It can also be used in the synthesis of Alatrofloxacin Mesylate (A511400).

Synthesis

Tert-butyl REL-(1R,5S,6S)-6-amino-3-azabicyclo[3.1.0]hexane-3-carboxylate was prepared by using tert-butyl chloroformate and 3-azabicyclo[3.1.0]hexan-6-amine as starting materials.

Take a dry three-necked reaction flask, one fitted with a calcium chloride desiccator, one fitted with a dropping funnel, and the tetrahydrofuran solution needs to be anhydrous in advance. Weigh the tert-butyl ester formyl chloride dissolved in 180mL of anhydrous tetrahydrofuran solution, start the stirring device. After dissolution, the solution was slowly added to 200 mL of tetrahydrofuran solution under ice-water bath conditions (3-azabicyclo[3.1.0]hexan-6-amine had been dissolved in tetrahydrofuran solution), and a solid precipitated immediately, and the stirring was continued for 4 hr at 35 ?? after the addition, and the progress of the reaction was detected by thin-layer chromatography. When the reaction was completed and the reaction solution was cooled, 400 mL of ice water was added to the reaction to make the product precipitate completely, and a light yellow solid was obtained by filtration. After drying and crystallization with anhydrous ethanol, tert-butyl REL-(1R,5S,6S)-6-amino-3-azabicyclo[3.1.0]hexane-3-carboxylate was obtained.

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