(1R,2S,3R,4S)-3-Amino-1,7,7-trimethylbicyclo[2.2.1]heptan-2-ol

Base Information

• Chemical Name: (1R,2S,3R,4S)-3-Amino-1,7,7-trimethylbicyclo[2.2.1]heptan-2-ol
• CAS No.: 41719-73-7
• Molecular Formula: C10H19NO
• Molecular Weight: 169.267
• DSSTox Substance ID: DTXSID90455343
• Nikkaji Number: J677.723F
• Wikidata: Q82277301
• Mol file: 41719-73-7.mol

Synonyms:41719-73-7;(1R,2S,3R,4S)-3-Amino-1,7,7-trimethylbicyclo[2.2.1]heptan-2-ol;CTK1D3684;DTXSID90455343;(4alpha)-1beta,7,7-Trimethyl-3alpha-aminobicyclo[2.2.1]heptane-2alpha-ol

Chemical Property of (1R,2S,3R,4S)-3-Amino-1,7,7-trimethylbicyclo[2.2.1]heptan-2-ol

Chemical Property:

• PSA: 46.25000
• LogP: 1.83100
• Solubility.: DCM, Methanol
• XLogP3: 1.1
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 0
• Exact Mass: 169.146664230
• Heavy Atom Count: 12
• Complexity: 214

Purity/Quality:

98%min ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1(C2CCC1(C(C2N)O)C)C
• Isomeric SMILES: C[C@@]12CC[C@@H](C1(C)C)[C@H]([C@H]2O)N
• Uses: (1R)-3-endo-Aminoborneol is an intermediate in the synthesis of Gibornuride (G409700), an anti-diabetic drug from the group of sulfonylureas.

Technology Process of (1R,2S,3R,4S)-3-Amino-1,7,7-trimethylbicyclo[2.2.1]heptan-2-ol

There total 8 articles about (1R,2S,3R,4S)-3-Amino-1,7,7-trimethylbicyclo[2.2.1]heptan-2-ol 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:

(1R,4S)-3-hydroxyimino-1,7,7-trimethylbicyclo[2.2.1]heptan-2-one (663-17-2,5338-41-0,13854-86-9,13854-87-0,22472-58-8,31571-14-9,103833-77-8) → (1R,2R,3S,4S)-3-Amino-1,7,7-trimethyl-bicyclo[2.2.1]heptan-2-ol (29900-93-4) + (2S)-3-exo-aminoisoborneol (41719-73-7)

Guidance literature:

With lithium aluminium tetrahydride; In diethyl ether; at 20 ℃;

DOI:10.1248/cpb.49.1018

Reference yield:

(1R,2S,4S)-2-exo-hydroxy-3-(hydroxyimino)-1,7,7-trimethylbicyclo<2.2.1>heptane (162425-97-0) → (1R,2R,3S,4S)-3-Amino-1,7,7-trimethyl-bicyclo[2.2.1]heptan-2-ol (29900-93-4) + (2S)-3-exo-aminoisoborneol (41719-73-7)

Guidance literature:

With lithium aluminium tetrahydride; In diethyl ether; Yield given. Yields of byproduct given;

Reference yield:

3-endo-aminobornan-2-one (33162-63-9) → (1R,2R,3S,4S)-3-Amino-1,7,7-trimethyl-bicyclo[2.2.1]heptan-2-ol (29900-93-4) + (2S)-3-exo-aminoisoborneol (41719-73-7)

Guidance literature:

With lithium aluminium tetrahydride;

upstream raw materials:

3-endo-aminobornan-2-one

(1R,2S,4S)-2-exo-hydroxy-3-(hydroxyimino)-1,7,7-trimethylbicyclo<2.2.1>heptane

(1R,4S)-3-hydroxyimino-1,7,7-trimethylbicyclo[2.2.1]heptan-2-one

Downstream raw materials:

N-<(1R,2S,3R,4S)-2-hydroxy-1,7,7-trimethylbucyclohept-3-yl>-3-(phenylthio)-2-<(phenylthio)methyl>propanamide

(1R,2S,3R,4S)-3-TsNH-1,7,7-(CH₃)3-bicyclo[2.2.1]heptan-2-ol

N-<(1R,2S,3R,4S)-2-hydroxy-1,7,7-trimethylbicyclo<2.2.1>heptan-3-yl>-2-<(S)-1-benzyloxycarbonyl>prolinamide

(1R,2S,3R,4S)-3-(4-vinylbenzenesulfonyl)amino-1,7,7-trimethylbicyclo[2.2.1]heptan-2-ol