(1R,2R,3S,5R)-2-Amino-2,6,6-trimethyl-bicyclo[3.1.1]heptane-3-carboxylic acid methyl ester

Base Information

• Chemical Name: (1R,2R,3S,5R)-2-Amino-2,6,6-trimethyl-bicyclo[3.1.1]heptane-3-carboxylic acid methyl ester
• CAS No.: 705949-02-6
• Molecular Formula: C₁₂H₂₁NO₂
• Molecular Weight: 211.304
• DSSTox Substance ID: DTXSID50588707
• Wikidata: Q82481558
• Mol file: 705949-02-6.mol

Synonyms:705949-02-6;(1R,2R,3S,5R)-2-Amino-2,6,6-trimethyl-bicyclo[3.1.1]heptane-3-carboxylic acid methyl ester;Methyl (1R,2R,3S,5R)-2-amino-2,6,6-trimethylbicyclo[3.1.1]heptane-3-carboxylate;DTXSID50588707

Chemical Property of (1R,2R,3S,5R)-2-Amino-2,6,6-trimethyl-bicyclo[3.1.1]heptane-3-carboxylic acid methyl ester

Chemical Property:

• Vapor Pressure: 0.0132mmHg at 25°C
• XLogP3: 1.9
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 2
• Exact Mass: 211.157228913
• Heavy Atom Count: 15
• Complexity: 300

Purity/Quality:

98%min ^*data from raw suppliers

(1R,2R,3S,5R)-2-AMINO-2,6,6-TRIMETHYL-BICYCLO(3.1.1)HEPTANE-3-CARBOXYLIC ACID METHYL ESTER 95.00% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: CC1(C2CC(C(C1C2)(C)N)C(=O)OC)C
• Isomeric SMILES: C[C@@]1([C@H](C[C@H]2C[C@@H]1C2(C)C)C(=O)OC)N

Technology Process of (1R,2R,3S,5R)-2-Amino-2,6,6-trimethyl-bicyclo[3.1.1]heptane-3-carboxylic acid methyl ester

There total 2 articles about (1R,2R,3S,5R)-2-Amino-2,6,6-trimethyl-bicyclo[3.1.1]heptane-3-carboxylic acid methyl ester 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: 75.0%

methanol (67-56-1) + (1S,2S,5R,7S)-2,8,8-trimethyl-3-azatricyclo[5.1.1.02,5]nonan-4-one (35182-62-8,328010-05-5) → C12H21NO2 (705949-09-3,705949-02-6)

Guidance literature:

With hydrogenchloride; at 80 ℃; for 1.5h; Microwave irradiation;

DOI:10.1055/s-0033-1339291

Reference yield:

(+)-α-pinene (7785-70-8,25766-18-1) → C12H21NO2 (705949-09-3,705949-02-6)

Guidance literature:

Multi-step reaction with 2 steps

1: sodium sulfite / 2 h

2: hydrogenchloride / 1.5 h / 80 °C / Microwave irradiation

With hydrogenchloride; sodium sulfite;

DOI:10.1055/s-0033-1339291

Reference yield:

C12H21NO2 (705949-02-6) → (1R,2R,7S,9R)-phenyl-(2,10,10-trimethyl-5-thia-3-azatricyclo[7.1.1.02,7]undec-4-ylidene)amine

Guidance literature:

Multi-step reaction with 3 steps

1: lithium aluminium tetrahydride

2: toluene / 20 °C

3: 1,1'-carbonyldiimidazole / tetrahydrofuran / 1 h / 125 °C / Microwave irradiation

With lithium aluminium tetrahydride; 1,1'-carbonyldiimidazole; In tetrahydrofuran; toluene;

DOI:10.3390/molecules191015918

upstream raw materials:

methanol

(1S,2S,5R,7S)-2,8,8-trimethyl-3-azatricyclo[5.1.1.0^2,5]nonan-4-one

(+)-α-pinene

Downstream raw materials:

1-((1R,2R,3S,5R)-3-Hydroxymethyl-2,6,6-trimethyl-bicyclo[3.1.1]hept-2-yl)-3-phenyl-thiourea

(1R,2R,3S,5R)-2-amino-3-hydroxymethyl-2,6,6-trimethylbicyclo[3.1.1]heptane