(S)-tert-butyl 3-oxo-1-phenylpropylcarbamate

Base Information

• Chemical Name: (S)-tert-butyl 3-oxo-1-phenylpropylcarbamate
• CAS No.: 135865-78-0
• Molecular Formula: C14H19NO3
• Molecular Weight: 249.31
• Mol file: 135865-78-0.mol

Synonyms:Carbamicacid, (3-oxo-1-phenylpropyl)-, 1,1-dimethylethyl ester, (S)-;Carbamic acid,[(1S)-3-oxo-1-phenylpropyl]-, 1,1-dimethylethyl ester (9CI);(S)-(3-Oxo-1-phenylpropyl)carbamic acid tert-butyl ester;(S)-3-Phenyl-3-Boc-aminopropionaldehyde;(S)-tert-Butyl(3-oxo-1-phenylpropyl)carbamate;tert-Butyl (1S)-3-oxo-1-phenylpropylcarbamate;

Chemical Property of (S)-tert-butyl 3-oxo-1-phenylpropylcarbamate

Chemical Property:

• Vapor Pressure: 9.96E-06mmHg at 25°C
• Refractive Index: 1.508
• Boiling Point: 371.9 °C at 760 mmHg
• PKA: 11.56±0.46(Predicted)
• Flash Point: 178.7 °C
• PSA: 55.40000
• Density: 1.075 g/cm³
• LogP: 3.23230
• Storage Temp.: Inert atmosphere,Store in freezer, under -20°C
• Solubility.: Chloroform, DMSO, Ethyl Acetate, Methanol

Purity/Quality:

98% ^*data from raw suppliers

N-Boc-(3S)-3-phenyl-3-aminopropionaldehyde ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Uses: (S)-tert-butyl 3-oxo-1-phenylpropylcarbamate is an intermediate used in the preparation of spirotropane compounds which are used as modulators of CCR5 chemokine receptors.

Technology Process of (S)-tert-butyl 3-oxo-1-phenylpropylcarbamate

There total 40 articles about (S)-tert-butyl 3-oxo-1-phenylpropylcarbamate 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: 95.0%

methyl (3S)-3-[(tert-butoxycarbonyl)amino]-3-phenylpropionate (190189-97-0) → tert-butyl (1S)-3-oxo-1-phenylpropylcarbamate (135865-78-0)

Guidance literature:

With diisobutylaluminium hydride; In toluene; at -78 ℃; for 0.333333h;

DOI:10.1021/acs.orglett.8b02087

Reference yield: 87.0%

acetaldehyde (75-07-0,9002-91-9) + benzaldehyde N-boc imine (150884-50-7) → tert-butyl (1S)-3-oxo-1-phenylpropylcarbamate (135865-78-0)

Guidance literature:

With N-(4,5-dihydro-3H-4-aza-cyclohepta[2,1-a;3,4-a']dinaphthalen-2-yl)-C,C,C-trifluoro-methanesulfonamide; at 0 ℃; for 4h; optical yield given as %ee; enantioselective reaction;

DOI:10.1002/anie.200805628

Reference yield: 87.0%

ethyl (3S)-3-{[(tert-butoxy)carbonyl]amino}-3-phenylpropanoate (167834-23-3) → tert-butyl (1S)-3-oxo-1-phenylpropylcarbamate (135865-78-0)

Guidance literature:

With diisobutylaluminium hydride; In dichloromethane; at -78 ℃;

DOI:10.1016/j.bmcl.2010.03.095

upstream raw materials:

(S)-N-(tert-Butoxycarbonyl)-1-phenyl-3-butenylamine

(S)-3-(N-tert-butoxycarbonylamino)-3-phenylpropanenitrile

methyl (3S)-3-[(tert-butoxycarbonyl)amino]-3-phenylpropionate

ethyl (3S)-3-{[(tert-butoxy)carbonyl]amino}-3-phenylpropanoate

Downstream raw materials:

methyl 1-({(3S)-3-[(tert-butoxycarbonyl)amino]-3-phenylpropyl}amino)cyclopentanecarboxylate

S-(3-hydroxy-1-phenyl-propyl)-carbamic acid tert-butyl ester

(S)-3-((1R,3R,5S)-3-(3-isopropyl-5-methyl-4H-1,2,4-triazol-4-yl)-8-azabicyclo[3.2.1]octan-8-yl)-1-phenylpropan-1-amine

maraviroc

Refernces

• 1、 Zou, Sijia,Li, Weiwei,Fu, Kai,Cao, Weidi,Lin, Lili,Feng, Xiaoming. "Chiral N,N′-Dioxide/Tm(OTf)3 Complex-Catalyzed Asymmetric Bisvinylogous Mannich Reaction of Silyl Ketene Acetal with Aldimines". . p. 2295 - 2300. Retrieved 2019.
• 2、 -. "Asymmetric synthesis method of chiral beta-amino aldehyde compound". Paragraph 0128-0133. . Retrieved 2020/03/11.
• 3、 Li, Dongmei,Tan, Yu,Peng, Lei,Li, Shan,Zhang, Nan,Liu, Yidong,Yan, Hailong. "Asymmetric Mannich Reaction and Construction of Axially Chiral Sulfone-Containing Styrenes in One Pot from α-Amido Sulfones Based on the Waste-Reuse Strategy". supporting information. p. 4959 - 4963. Retrieved 2018/08/24.