N-Boc-L-trans-4,5-methanoproline ethyl ester

Base Information

Chemical Name:N-Boc-L-trans-4,5-methanoproline ethyl ester
CAS No.:214193-10-9
Molecular Formula:C₁₃H₂₁NO₄
Molecular Weight:255.314
Hs Code.:
Mol file:214193-10-9.mol

Synonyms:2-aza-bicyclo[3.1.0]hexane-2,3-dicarboxylic acid 2-tert-butyl ester 3-ethyl ester

Suppliers and Price of N-Boc-L-trans-4,5-methanoproline ethyl ester

Supply Marketing:

Business phase:: The product has achieved commercial mass production^*data from LookChem market partment

Manufacturers and distributors:

Manufacture/Brand
Chemicals and raw materials
Packaging
price

TRC
N-Boc-L-trans-4,5-methanoprolineEthylEster
10mg
$ 525.00

Total 6 raw suppliers

Chemical Property of N-Boc-L-trans-4,5-methanoproline ethyl ester

Chemical Property:

Purity/Quality:

98%, ^*data from raw suppliers

N-Boc-L-trans-4,5-methanoprolineEthylEster ^*data from reagent suppliers

Safty Information:

Pictogram(s):
Hazard Codes:

MSDS Files:

Useful:

Uses N-Boc-L-trans-4,5-methanoproline Ethyl Ester is an impurity of the drug Saxagliptin (S143500), a potent and selective reversible inhibitor of dipeptidyl peptidase-4.

Technology Process of N-Boc-L-trans-4,5-methanoproline ethyl ester

There total 4 articles about N-Boc-L-trans-4,5-methanoproline ethyl 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: 11.0%

: 75-11-6
diiodomethane

: 178172-26-4
(5S)-4,5-dihydro-1H-pyrrol-1,5-dicarboxylic acid [1-(1,1-dimethylethyl)] 5-ethyl ester

: 214193-10-9
2-aza-bicyclo[3.1.0]hexane-2,3-dicarboxylic acid 2-tert-butyl ester 3-ethyl ester

: 214193-11-0
(1S,3S,5S)-2-(tert-butoxycarbonyl)-2-azabicyclo[3.1.0]hexane-3-formic acid ethyl ester

Guidance literature:: With diethylzinc; In 1,2-dimethoxyethane; dichloromethane; toluene; at -30 - 20 ℃;
DOI:10.1016/j.bmc.2013.12.061

Reference yield:

: 24424-99-5
di-tert-butyl dicarbonate

: (S)-2-Aza-bicyclo[3.1.0]hexane-3-carboxylic acid ethyl ester

: 214193-10-9
2-aza-bicyclo[3.1.0]hexane-2,3-dicarboxylic acid 2-tert-butyl ester 3-ethyl ester

: 214193-11-0
(1S,3S,5S)-2-(tert-butoxycarbonyl)-2-azabicyclo[3.1.0]hexane-3-formic acid ethyl ester

Guidance literature:: With dmap; triethylamine; In dichloromethane; Yield given. Yields of byproduct given;
DOI:10.1016/S0960-894X(98)00377-1

Reference yield:

: 144978-35-8,144978-12-1,251924-83-1
(S)-ethyl N-tert-butoxycarbonylpyroglutamate

: 214193-10-9
2-aza-bicyclo[3.1.0]hexane-2,3-dicarboxylic acid 2-tert-butyl ester 3-ethyl ester

: 214193-11-0
(1S,3S,5S)-2-(tert-butoxycarbonyl)-2-azabicyclo[3.1.0]hexane-3-formic acid ethyl ester

Guidance literature:: Multi-step reaction with 3 steps

1: lithium triethylborohydride / tetrahydrofuran / 1 h / -10 °C

2: trifluoroacetic anhydride; N-ethyl-N,N-diisopropylamine / toluene / 13 h / 0 - 110 °C

3: diethylzinc / dichloromethane; toluene / 4 h / 0 - 20 °C

With diethylzinc; lithium triethylborohydride; N-ethyl-N,N-diisopropylamine; trifluoroacetic anhydride; In tetrahydrofuran; dichloromethane; toluene;
DOI:10.1021/acs.jmedchem.9b00790