tert-Butyl (2-phenylcyclopropyl)carbamate

Base Information

• Chemical Name: tert-Butyl (2-phenylcyclopropyl)carbamate
• CAS No.: 185256-47-7
• Molecular Formula: C₁₄H₁₉NO₂
• Molecular Weight: 233.31
• Mol file: 185256-47-7.mol

Synonyms:(-)-(1R,2S)-trans (2-phenyl-cyclopropyl)carbaminic acid tert-butyl ester

Chemical Property of tert-Butyl (2-phenylcyclopropyl)carbamate

Chemical Property:

• Storage Temp.: 2-8°C

Purity/Quality:

97% ^*data from raw suppliers

tert-Butyl((1R,2S)-2-phenylcyclopropyl)carbamate 97% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of tert-Butyl (2-phenylcyclopropyl)carbamate

There total 16 articles about tert-Butyl (2-phenylcyclopropyl)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: 80.0%

di-tert-butyl dicarbonate (24424-99-5) + (1R,2S)-1-amino-2-phenylcyclopropane (95-62-5,155-09-9,3721-26-4,3721-28-6,13531-35-6,24873-95-8,69684-88-4,69684-89-5,54-97-7) → (-)-(1R,2S)-trans (2-phenyl-cyclopropyl)carbaminic acid tert-butyl ester (185256-47-7,847644-86-4)

Guidance literature:

di-tert-butyl dicarbonate; (1R,2S)-1-amino-2-phenylcyclopropane; In dichloromethane; at 20 ℃; for 2.5h; Cooling with ice; Inert atmosphere;

With potassium carbonate; In dichloromethane; at 20 ℃; for 2h; Inert atmosphere;

DOI:10.1016/j.bmcl.2021.127993

Reference yield: 72.0%

(1R,2R)-trans-2-phenyl-1-cyclopropanecarboxylic acid (3471-10-1) + tert-butyl alcohol (75-65-0) → (-)-(1R,2S)-trans (2-phenyl-cyclopropyl)carbaminic acid tert-butyl ester (185256-47-7,847644-86-4)

Guidance literature:

With diphenyl phosphoryl azide; triethylamine; at 90 ℃; for 5h;

Reference yield: 51.0%

(1R,2R)-trans-2-phenyl-1-cyclopropanecarboxylic acid (3471-10-1) → (-)-(1R,2S)-trans (2-phenyl-cyclopropyl)carbaminic acid tert-butyl ester (185256-47-7,847644-86-4) + (-)-(1R,2S)-trans (2-phenyl-cyclopropyl)-carbamoyl azide

Guidance literature:

With diphenyl phosphoryl azide; triethylamine; In tert-butyl alcohol; at 90 - 95 ℃; for 5h;

DOI:10.1016/S0957-4166(96)00457-0

upstream raw materials:

(1R,2R)-trans-2-phenyl-1-cyclopropanecarboxylic acid

tert-butyl alcohol

(1S,2S)-2-phenylcyclopropane-1-carboxylic acid

ethyl (S,S)-2-phenylcyclopropane-1-carboxylate

Downstream raw materials:

(1R,2S)-1-amino-2-phenylcyclopropane

(1S,2R)-tranylcypromine

tranylcypromine hydrochloride

Refernces

• 1、 Huang, Ming-Jie,Guo, Jia-Wen,Fu, Yun-Dong,You, Ya-Zhen,Xu, Wen-Yu,Song, Ting-Yu,Li, Ran,Chen, Zi-Tong,Huang, Li-Hua,Liu, Hong-Min. "Discovery of new tranylcypromine derivatives as highly potent LSD1 inhibitors". supporting information. . Retrieved 2021/04/12.
• 2、 Ishizuka, Yuki,Fujimori, Hirohisa,Noguchi, Takuya,Kawasaki, Masashi,Kishida, Mari,Nagai, Takuya,Imai, Nobuyuki,Kirihara, Masayuki. "Asymmetric syntheses of pharmaceuticals containing a cyclopropane moiety using catalytic asymmetric Simmons-Smith reactions of allylalcohols: Syntheses of optically active tranylcypromine and milnacipran". . p. 1311 - 1313. Retrieved 2013/10/22.