(1S,4R)-N-(benzyloxycarbonyl)-7-azabicyclo[2.2.1]heptan-3-one-1-carboxylic acid

Base Information

• Chemical Name: (1S,4R)-N-(benzyloxycarbonyl)-7-azabicyclo[2.2.1]heptan-3-one-1-carboxylic acid
• CAS No.: 182138-13-2
• Molecular Formula: C₁₅H₁₅NO₅
• Molecular Weight: 289.288
• Mol file: 182138-13-2.mol

Synonyms:(1S,4R)-N-(benzyloxycarbonyl)-7-azabicyclo[2.2.1]heptan-3-one-1-carboxylic acid

Chemical Property of (1S,4R)-N-(benzyloxycarbonyl)-7-azabicyclo[2.2.1]heptan-3-one-1-carboxylic acid

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (1S,4R)-N-(benzyloxycarbonyl)-7-azabicyclo[2.2.1]heptan-3-one-1-carboxylic acid

There total 10 articles about (1S,4R)-N-(benzyloxycarbonyl)-7-azabicyclo[2.2.1]heptan-3-one-1-carboxylic acid 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: 100.0%

(1S,4R)-3-Oxo-7-aza-bicyclo[2.2.1]heptane-1,7-dicarboxylic acid 7-benzyl ester 1-tert-butyl ester (182137-75-3) → (1S,4R)-N-(benzyloxycarbonyl)-7-azabicyclo[2.2.1]heptan-3-one-1-carboxylic acid (182138-13-2)

Guidance literature:

With trifluoroacetic acid; In dichloromethane; for 48h;

DOI:10.1021/jo960759m

Reference yield:

(1S,4R)-3-Hydroxy-7-aza-bicyclo[2.2.1]heptane-1,7-dicarboxylic acid 7-benzyl ester 1-tert-butyl ester → (1S,4R)-N-(benzyloxycarbonyl)-7-azabicyclo[2.2.1]heptan-3-one-1-carboxylic acid (182138-13-2)

Guidance literature:

Multi-step reaction with 2 steps

1: 1.) oxalyl chloride, DMSO, 2.) Et₃N / 1.) CH₂Cl₂, -78 deg C, 1 h, 2.) -78 deg C, 30 min; room temperature, 1 h.

2: 100 percent / TFA / CH₂Cl₂ / 48 h

With oxalyl dichloride; dimethyl sulfoxide; triethylamine; trifluoroacetic acid; In dichloromethane;

DOI:10.1021/jo960759m

Reference yield:

(+)-(1'R,2'S,5'R)-8'-phenylmenthyl (1S,5S,8S)-3-methyl-exo-8-iodo-2-oxa-4-azabicyclo<3.3.1>non-3-ene-5-carboxylate (176965-95-0) → (1S,4R)-N-(benzyloxycarbonyl)-7-azabicyclo[2.2.1]heptan-3-one-1-carboxylic acid (182138-13-2)

Guidance literature:

Multi-step reaction with 8 steps

1: 99 percent / tetrahydrofuran; H₂O / 5 h / 20 °C

2: 95 percent / Na₂CO₃ / ethanol / 24 h / 30 °C

3: 94 percent / aq. 6N HCl / 14 h / Heating

4: 100 percent / CH₃COCl / 12 h / 60 °C

5: 85 percent / DIEA / acetonitrile / 24 h / 50 °C

6: 91 percent / (COCl)2; DMSO / CH₂Cl₂ / 0.33 h / -78 °C

7: 6N HCl / 14 h / Heating

8: H₂O / 36 h / 35 °C

With hydrogenchloride; oxalyl dichloride; sodium carbonate; dimethyl sulfoxide; N-ethyl-N,N-diisopropylamine; acetyl chloride; In tetrahydrofuran; ethanol; dichloromethane; water; acetonitrile; 1: Hydrolysis / 2: Cyclization / 3: Hydrolysis / 4: Esterification / 5: Acylation / 6: Oxidation / 7: Hydrolysis / 8: Acylation;

DOI:10.1016/S0957-4166(99)00408-5

upstream raw materials:

(1S,4R)-3-Oxo-7-aza-bicyclo[2.2.1]heptane-1,7-dicarboxylic acid 7-benzyl ester 1-tert-butyl ester

benzyl chloroformate

(+)-(1'R,2'S,5'R)-8'-phenylmenthyl (1S,5S,8S)-3-methyl-exo-8-iodo-2-oxa-4-azabicyclo<3.3.1>non-3-ene-5-carboxylate

methyl (1S,3S,4R)-N-(tert-butoxycarbonyl)-3-hydroxy-7-azabicyclo[2.2.1]heptane-1-carboxylate

Downstream raw materials:

(1R,4S)-2-Oxo-7-aza-bicyclo[2.2.1]heptane-7-carboxylic acid benzyl ester

(-)-(1R,4S)-tert-butyl 2-oxo-7-azabicyclo[2.2.1]heptane-7-carboxylate