2-Azabicyclo[3.1.0]hexane-3-carbonitrile, 2-[(2S)-2-aMino-2-(3-hydroxytricyclo[3.3.1.13,7]dec-1-yl)acetyl]-, (1R,3R,5R)-

Base Information

• Chemical Name: 2-Azabicyclo[3.1.0]hexane-3-carbonitrile, 2-[(2S)-2-aMino-2-(3-hydroxytricyclo[3.3.1.13,7]dec-1-yl)acetyl]-, (1R,3R,5R)-
• CAS No.: 1564265-94-6
• Molecular Formula: C₁₈H₂₅N₃O₂
• Molecular Weight: 315.415
• Mol file: 1564265-94-6.mol

Synonyms:(S)-3-hydroxyadamantylglycine-D-cis-4,5-methanoprolinenitrile

Chemical Property of 2-Azabicyclo[3.1.0]hexane-3-carbonitrile, 2-[(2S)-2-aMino-2-(3-hydroxytricyclo[3.3.1.13,7]dec-1-yl)acetyl]-, (1R,3R,5R)-

Chemical Property:

• Boiling Point: 548.7±35.0 °C(Predicted)
• PKA: 15.12±0.40(Predicted)
• Density: 1.35±0.1 g/cm3(Predicted)

Purity/Quality:

99% ^*data from raw suppliers

(2’S,2R,cis)-Saxagliptin ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Uses: (2’S,2R,cis)-Saxagliptin is an impurity of Saxagliptin (S143500); a potent and selective reversible inhibitor of dipeptidyl peptidase-4 (DPP-IV) developed for the treatment of type 2 diabetes.

Technology Process of 2-Azabicyclo[3.1.0]hexane-3-carbonitrile, 2-[(2S)-2-aMino-2-(3-hydroxytricyclo[3.3.1.13,7]dec-1-yl)acetyl]-, (1R,3R,5R)-

There total 13 articles about 2-Azabicyclo[3.1.0]hexane-3-carbonitrile, 2-[(2S)-2-aMino-2-(3-hydroxytricyclo[3.3.1.13,7]dec-1-yl)acetyl]-, (1R,3R,5R)- which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 82.0%

(S)-N-Boc-3-hydroxyadamantylglycine-D-cis-4,5-methanoprolinenitrile (1564266-94-9) → (S)-3-hydroxyadamantylglycine-D-cis-4,5-methanoprolinenitrile (1564265-94-6,1564265-93-5)

Guidance literature:

With hydrogenchloride; In water; isopropyl alcohol; at 65 ℃; for 1.5h;

DOI:10.1016/j.bmc.2013.12.061

Reference yield:

ethyl (R)-2-pyrrolidone-5-carboxylate (68766-96-1) → (S)-3-hydroxyadamantylglycine-D-cis-4,5-methanoprolinenitrile (1564265-94-6,1564265-93-5)

Guidance literature:

Multi-step reaction with 10 steps

1.1: dmap

2.1: lithium triethylborohydride / toluene / -70 - -60 °C

3.1: dmap; trifluoroacetic anhydride; N-ethyl-N,N-diisopropylamine

4.1: water; lithium hydroxide / ethanol

5.1: ammonia; N-ethyl-N,N-diisopropylamine; methanesulfonyl chloride / tetrahydrofuran

6.1: diethylzinc / 1,2-dimethoxyethane; dichloromethane / -30 - 20 °C

7.1: isopropyl alcohol / 60 °C

8.1: benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine / ethyl acetate; acetonitrile / 3 h

9.1: trifluoroacetic anhydride; pyridine / tetrahydrofuran / 0.5 h / 0 °C

9.2: 18 h / 20 °C

10.1: hydrogenchloride / isopropyl alcohol; water / 1.5 h / 65 °C

With pyridine; hydrogenchloride; dmap; ammonia; water; diethylzinc; lithium triethylborohydride; benzotriazol-1-ol; methanesulfonyl chloride; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine; trifluoroacetic anhydride; lithium hydroxide; In tetrahydrofuran; 1,2-dimethoxyethane; ethanol; dichloromethane; water; ethyl acetate; isopropyl alcohol; toluene; acetonitrile; 6.1: |Simmons-Smith Cyclopropanation;

DOI:10.1016/j.bmc.2013.12.061

Reference yield:

(R)-N-((S)-(adamantan-1-yl)(carboxy)methyl)-2-hydroxy-1-phenylethan-1-ammonium chloride → (S)-3-hydroxyadamantylglycine-D-cis-4,5-methanoprolinenitrile (1564265-94-6,1564265-93-5)

Guidance literature:

Multi-step reaction with 6 steps

1.1: hydrogen; palladium 10% on activated carbon / acetic acid

2.1: triethylamine / methanol

3.1: potassium permanganate; potassium hydroxide / 90 °C

4.1: benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine / ethyl acetate; acetonitrile / 3 h

5.1: trifluoroacetic anhydride; pyridine / tetrahydrofuran / 0.5 h / 0 °C

5.2: 18 h / 20 °C

6.1: hydrogenchloride / isopropyl alcohol; water / 1.5 h / 65 °C

With pyridine; hydrogenchloride; potassium permanganate; palladium 10% on activated carbon; hydrogen; benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine; N-ethyl-N,N-diisopropylamine; trifluoroacetic anhydride; potassium hydroxide; In tetrahydrofuran; methanol; water; acetic acid; ethyl acetate; isopropyl alcohol; acetonitrile;

DOI:10.1016/j.bmc.2013.12.061

upstream raw materials:

(S)-N-Boc-3-hydroxyadamantylglycine-D-cis-4,5-methanoprolinenitrile

(S)-(+)-(adamant-1-yl)aminoacetic acid hydrochloride

1-tert-butyl 2-ethyl (2R)-5-hydroxypyrrolidine-1,2-dicarboxylate

1-tert-butyl 2-ethyl (2R)-2,3-dihydro-1H-pyrrole-1,2-dicarboxylate