(1α,5α,6α)-6-tert-butoxycarbonylamino-3-aza-bicyclo[3.1.0]hexane-3-carboxylic acid benzyl ester

Base Information

• Chemical Name: (1α,5α,6α)-6-tert-butoxycarbonylamino-3-aza-bicyclo[3.1.0]hexane-3-carboxylic acid benzyl ester
• CAS No.: 146726-08-1
• Molecular Formula: C₁₈H₂₄N₂O₄
• Molecular Weight: 332.4
• Mol file: 146726-08-1.mol

Synonyms:(1α,5α,6α)-6-tert-butoxycarbonylamino-3-aza-bicyclo[3.1.0]hexane-3-carboxylic acid benzyl ester

Chemical Property of (1α,5α,6α)-6-tert-butoxycarbonylamino-3-aza-bicyclo[3.1.0]hexane-3-carboxylic acid benzyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (1α,5α,6α)-6-tert-butoxycarbonylamino-3-aza-bicyclo[3.1.0]hexane-3-carboxylic acid benzyl ester

There total 11 articles about (1α,5α,6α)-6-tert-butoxycarbonylamino-3-aza-bicyclo[3.1.0]hexane-3-carboxylic acid benzyl 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:

tert-butyl alcohol (75-65-0) + (1α,5α,6α)-3-(benzyloxycarbonyl)-3-azabicyclo[3.1.0]hexane-6-carboxylic acid (134575-15-8) → (1α,5α,6α)-6-tert-butoxycarbonylamino-3-aza-bicyclo[3.1.0]hexane-3-carboxylic acid benzyl ester (146726-08-1)

Guidance literature:

With diphenyl phosphoryl azide; triethylamine; for 44h; Heating;

DOI:10.1016/j.bmcl.2004.03.070

Reference yield:

benzyl chloroformate (501-53-1,94274-21-2) + tert-butyl (1R,5S,6R)-3-azabicyclo[3.1.0]hexan-6-ylcarbamate (134575-17-0) → (1α,5α,6α)-6-tert-butoxycarbonylamino-3-aza-bicyclo[3.1.0]hexane-3-carboxylic acid benzyl ester (146726-08-1)

Guidance literature:

With triethylamine; In dichloromethane; at 0 - 20 ℃;

Reference yield:

ethyl (1α,5α,6α)-3-benzyl-3-azabicyclo[3.1.0]hexane-2,4-dione-6-carboxylate (134575-06-7,846024-42-8) → (1α,5α,6α)-6-tert-butoxycarbonylamino-3-aza-bicyclo[3.1.0]hexane-3-carboxylic acid benzyl ester (146726-08-1)

Guidance literature:

Multi-step reaction with 5 steps

1: LiAlH₄ / tetrahydrofuran / 48 h / Heating

2: H₂ / Pd/C / methanol / 23 h / 0 °C

3: aq. K₂CO₃ / dioxane / 15 h / 20 °C

4: CrO₃; aq. H₂SO₄ / acetone / 2 h / 0 - 20 °C

5: NEt₃; (PhO)2P(O)N₃ / 44 h / Heating

With chromium(VI) oxide; lithium aluminium tetrahydride; sulfuric acid; diphenyl phosphoryl azide; hydrogen; potassium carbonate; triethylamine; palladium on activated charcoal; In tetrahydrofuran; 1,4-dioxane; methanol; acetone; 4: Jones oxidation;

DOI:10.1016/j.bmcl.2004.03.070

upstream raw materials:

tert-butyl alcohol

(1α,5α,6α)-3-(benzyloxycarbonyl)-3-azabicyclo[3.1.0]hexane-6-carboxylic acid

3-benzyl 6-ethyl (1α,5α,6α)-3-azabicyclo[3.1.0]hexane-3,6-dicarboxylate

1-carboxybenzyl-3-pyrrolidine

Downstream raw materials:

tert-butyl (1R,5S,6R)-3-azabicyclo[3.1.0]hexan-6-ylcarbamate

(1α,5α,6α)-3-(2,6-difluoro-4-nitrophenyl)-3-azabicyclo[3.1.0]hexane-6-carboxylic acid tert-butyl ester

(1S,5R,6R)-3-(4-Amino-2,6-difluoro-phenyl)-3-aza-bicyclo[3.1.0]hexane-6-carboxylic acid tert-butyl ester

(R)-(1α,5α,6α)-3-[2,6-difluoro-4-(5-hydroxymethyl-2-oxooxazolidin-3-yl)phenyl]-3-azabicyclo[3.1.0]hexane-6-carboxylic acid tert-butyl ester