tert-Butyl(3-formylbicyclo[1.1.1]pentan-1-yl)carbamate

Base Information

• Chemical Name: tert-Butyl(3-formylbicyclo[1.1.1]pentan-1-yl)carbamate
• CAS No.: 1638771-06-8
• Molecular Formula: C₁₁H₁₇NO₃
• Molecular Weight: 211.261
• Hs Code.: 2924297099
• Mol file: 1638771-06-8.mol

Synonyms:

Chemical Property of tert-Butyl(3-formylbicyclo[1.1.1]pentan-1-yl)carbamate

Chemical Property:

Purity/Quality:

99%, ^*data from raw suppliers

N-(3-Formylbicyclo[1.1.1]pent-1-yl)-1,1-DimethylethylEsterCarbamicAcid ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Uses: Used in the preparation of bicyclic compounds that are useful as EP4 receptor antagonists in the treatment of cancer

Technology Process of tert-Butyl(3-formylbicyclo[1.1.1]pentan-1-yl)carbamate

There total 4 articles about tert-Butyl(3-formylbicyclo[1.1.1]pentan-1-yl)carbamate 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: 94.0%

(3-(hydroxymethyl)bicyclo[1.1.1]pent-1-yl)carbamic acid tert-butyl ester (1638765-26-0) → tert-butyl (3-formyl bicyclo[1.1.1]pentan-1-yl)carbamate (1638771-06-8)

Guidance literature:

With oxalyl dichloride; dimethyl sulfoxide; triethylamine; In dichloromethane; at -78 ℃; for 0.5h; Inert atmosphere;

Reference yield:

3-((tert-butoxycarbonyl)amino)bicyclo[1.1.1]pentane-1-carboxylic acid methyl ester (676371-64-5) → tert-butyl (3-formyl bicyclo[1.1.1]pentan-1-yl)carbamate (1638771-06-8)

Guidance literature:

Multi-step reaction with 3 steps

1.1: sodium hydroxide

2.1: dimethylsulfide borane complex / diethyl ether / 1 h / 0 - 20 °C

3.1: dimethyl sulfoxide; oxalyl dichloride / dichloromethane / 0.5 h / -60 °C

3.2: 0.5 h / -60 °C

With oxalyl dichloride; dimethylsulfide borane complex; dimethyl sulfoxide; sodium hydroxide; In diethyl ether; dichloromethane; 3.1: |Swern Oxidation / 3.2: |Swern Oxidation;

DOI:10.1002/ejoc.201701296

Reference yield:

3-((tert-butoxycarbonyl)amino)bicyclo[1.1.1]pentane-1-carboxylic acid (303752-38-7) → tert-butyl (3-formyl bicyclo[1.1.1]pentan-1-yl)carbamate (1638771-06-8)

Guidance literature:

Multi-step reaction with 2 steps

1.1: dimethylsulfide borane complex / diethyl ether / 1 h / 0 - 20 °C

2.1: dimethyl sulfoxide; oxalyl dichloride / dichloromethane / 0.5 h / -60 °C

2.2: 0.5 h / -60 °C

With oxalyl dichloride; dimethylsulfide borane complex; dimethyl sulfoxide; In diethyl ether; dichloromethane; 2.1: |Swern Oxidation / 2.2: |Swern Oxidation;

DOI:10.1002/ejoc.201701296

upstream raw materials:

(3-(hydroxymethyl)bicyclo[1.1.1]pent-1-yl)carbamic acid tert-butyl ester

3-((tert-butoxycarbonyl)amino)bicyclo[1.1.1]pentane-1-carboxylic acid

3-((tert-butoxycarbonyl)amino)bicyclo[1.1.1]pentane-1-carboxylic acid methyl ester

3‐(methoxycarbonyl)bicyclo[1.1.1]pentane‐1‐carboxylic acid

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