(1S,4R)-2alpha-Hydroxy-7-azabicyclo[2.2.1]heptane-7-carboxylic acid tert-butyl ester

Base Information

• Chemical Name: (1S,4R)-2alpha-Hydroxy-7-azabicyclo[2.2.1]heptane-7-carboxylic acid tert-butyl ester
• CAS No.: 154905-38-1
• Molecular Formula: C₁₁H₁₉NO₃
• Molecular Weight: 213.277
• DSSTox Substance ID: DTXSID801119791
• Nikkaji Number: J840.387B
• Mol file: 154905-38-1.mol

Synonyms:DTXSID801119791;EN300-39872511;(1S,4R)-2alpha-Hydroxy-7-azabicyclo[2.2.1]heptane-7-carboxylic acid tert-butyl ester;rac-tert-butyl (1R,2S,4S)-2-hydroxy-7-azabicyclo[2.2.1]heptane-7-carboxylate;154905-38-1;7-Azabicyclo[2.2.1]heptane-7-carboxylic acid, 2-hydroxy-, 1,1-dimethylethyl ester, (1S-exo)-

Chemical Property of (1S,4R)-2alpha-Hydroxy-7-azabicyclo[2.2.1]heptane-7-carboxylic acid tert-butyl ester

Chemical Property:

• XLogP3: 1.2
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 2
• Exact Mass: 213.13649347
• Heavy Atom Count: 15
• Complexity: 272

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: CC(C)(C)OC(=O)N1C2CCC1C(C2)O
• Isomeric SMILES: CC(C)(C)OC(=O)N1[C@@H]2CC[C@H]1[C@@H](C2)O

Technology Process of (1S,4R)-2alpha-Hydroxy-7-azabicyclo[2.2.1]heptane-7-carboxylic acid tert-butyl ester

There total 16 articles about (1S,4R)-2alpha-Hydroxy-7-azabicyclo[2.2.1]heptane-7-carboxylic acid tert-butyl 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: 97.0%

(1S,2R,4R)-2-((S)-3,3,3-Trifluoro-2-methoxy-2-phenyl-propionyloxy)-7-aza-bicyclo[2.2.1]heptane-7-carboxylic acid tert-butyl ester (154905-37-0) → (+)-exo-7-<(1,1-Domethylethoxy)carbonyl>-7-azabicyclo<2.2.1>heptan-2-ol (154905-38-1,152533-46-5,154905-36-9)

Guidance literature:

With potassium hydroxide; In ethanol; for 2h; Ambient temperature;

DOI:10.1021/jo00086a030

Reference yield: 28.0%

(1S,4R)-7-(tert-Butoxycarbonyl)-7-azabicyclo<2.2.1>heptan-2-one (163513-99-3,163513-98-2) → 7-<(1,1-dimethylethoxy)carbonyl>-7-azabicyclo<2.2.1>heptan-2-endo-ol (152533-46-5,154905-36-9) + (+)-exo-7-<(1,1-Domethylethoxy)carbonyl>-7-azabicyclo<2.2.1>heptan-2-ol (154905-38-1,152533-46-5,154905-36-9)

Guidance literature:

With hydrogen; triethylamine; platinum(IV) oxide; In ethanol; at 20 ℃; for 48h;

Reference yield:

N-<(Trifluoroacetyl)amino>cyclohex-3-ene (78293-47-7) → (+)-exo-7-<(1,1-Domethylethoxy)carbonyl>-7-azabicyclo<2.2.1>heptan-2-ol (154905-38-1,152533-46-5,154905-36-9)

Guidance literature:

Multi-step reaction with 8 steps

1: 66 percent / Cs₂CO₃ / dimethylformamide / 40 h / 70 °C

2: 80percent m-CPBA / CH₂Cl₂ / 4 h / Ambient temperature

3: 78 percent / aq. K₂CO₃ / methanol / 72 h / Ambient temperature

4: 48 percent / 1-methyl-2-pyrrolidinone / 16 h / 180 °C

5: 5 N HCl, H₂ / Pd(OH)2/C / ethanol / 6 h / 40 °C / 2068.6 Torr

6: 1 N NaOH / dioxane / 18 h / Ambient temperature

7: 43 percent / DMAP / CH₂Cl₂ / 18 h / Ambient temperature

8: 97 percent / KOH / ethanol / 2 h / Ambient temperature

With 1-methyl-pyrrolidin-2-one; hydrogenchloride; dmap; potassium hydroxide; sodium hydroxide; hydrogen; potassium carbonate; caesium carbonate; 3-chloro-benzenecarboperoxoic acid; palladium dihydroxide; In 1,4-dioxane; methanol; ethanol; dichloromethane; N,N-dimethyl-formamide;

DOI:10.1021/jo00086a030

upstream raw materials:

(1S,2R,4R)-2-((S)-3,3,3-Trifluoro-2-methoxy-2-phenyl-propionyloxy)-7-aza-bicyclo[2.2.1]heptane-7-carboxylic acid tert-butyl ester

7-tert-butoxycarbonyl-7-azabicyclo<2.2.1>heptane

di-tert-butyl dicarbonate

N-<(Trifluoroacetyl)amino>cyclohex-3-ene

Downstream raw materials:

(1S,4R)-7-(tert-Butoxycarbonyl)-7-azabicyclo<2.2.1>heptan-2-one

(-)-epibatidine