(1S)-2-[(2S)-2-(benzyl-tert-butoxycarbonylamino)propylidene]cyclopentanecarboxylic acid methyl ester

Base Information

• Chemical Name: (1S)-2-[(2S)-2-(benzyl-tert-butoxycarbonylamino)propylidene]cyclopentanecarboxylic acid methyl ester
• CAS No.: 930579-59-2
• Molecular Formula: C₂₂H₃₁NO₄
• Molecular Weight: 373.492
• Mol file: 930579-59-2.mol

Synonyms:(1S)-2-[(2S)-2-(benzyl-tert-butoxycarbonylamino)propylidene]cyclopentanecarboxylic acid methyl ester

Chemical Property of (1S)-2-[(2S)-2-(benzyl-tert-butoxycarbonylamino)propylidene]cyclopentanecarboxylic acid methyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (1S)-2-[(2S)-2-(benzyl-tert-butoxycarbonylamino)propylidene]cyclopentanecarboxylic acid methyl ester

There total 15 articles about (1S)-2-[(2S)-2-(benzyl-tert-butoxycarbonylamino)propylidene]cyclopentanecarboxylic acid methyl 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:

(5S,6S)-1-Benzyl-5-(tert-butyl-dimethyl-silanyloxy)-6-methyl-piperidine-2,4-dione → (1S)-2-[(2S)-2-(benzyl-tert-butoxycarbonylamino)propylidene]cyclopentanecarboxylic acid methyl ester (930579-59-2)

Guidance literature:

Multi-step reaction with 11 steps

1: 2.41 g / triethylamine / CH₂Cl₂ / 10 h / 20 °C

2: 90.7 percent / Pd[P(o-Tol)3]2Cl₂ / tetrahydrofuran / 1 h / 20 °C

3: 98.7 percent / sodium borohydride / methanol; tetrahydrofuran / 12 h / 0 °C

4: 4-(dimethylamino)pyridine; pyridine / CH₂Cl₂ / 12 h / 20 °C

5: hexafluorosilicic acid / acetonitrile; methanol; H₂O / 3 h / 40 °C

6: 4-(dimethylamino)pyridine; pyridine / CHCl₃

7: NaI / acetone

8: 70.1 percent / SmI₂; N,N-dimethylpropyleneurea / acetonitrile / 0.05 h / -18 °C

9: 1,2-dichloro-ethane / 3 h / 20 °C

10: triflic acid; H₂O / tetrahydrofuran / 3 h

11: 42.8 mg / diisopropylethylamine / dimethylformamide / 2 h

With pyridine; dmap; 1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone; sodium tetrahydroborate; fluorosilicic acid; samarium diiodide; trifluorormethanesulfonic acid; water; triethylamine; N-ethyl-N,N-diisopropylamine; sodium iodide; dichlorobis(tri-O-tolylphosphine)palladium; In tetrahydrofuran; methanol; dichloromethane; chloroform; water; 1,2-dichloro-ethane; N,N-dimethyl-formamide; acetone; acetonitrile;

DOI:10.1016/j.tet.2006.12.055

Reference yield:

(2S,3S)-3-(benzylethoxycarbonylacetylamino)-2-(tert-butyldimethylsilanyloxy)butyric acid ethyl ester (930579-51-4) → (1S)-2-[(2S)-2-(benzyl-tert-butoxycarbonylamino)propylidene]cyclopentanecarboxylic acid methyl ester (930579-59-2)

Guidance literature:

Multi-step reaction with 13 steps

1: NaOEt / ethanol / 0.75 h / cooling

2: H₂O / acetonitrile / 2 h / Heating

3: 2.41 g / triethylamine / CH₂Cl₂ / 10 h / 20 °C

4: 90.7 percent / Pd[P(o-Tol)3]2Cl₂ / tetrahydrofuran / 1 h / 20 °C

5: 98.7 percent / sodium borohydride / methanol; tetrahydrofuran / 12 h / 0 °C

6: 4-(dimethylamino)pyridine; pyridine / CH₂Cl₂ / 12 h / 20 °C

7: hexafluorosilicic acid / acetonitrile; methanol; H₂O / 3 h / 40 °C

8: 4-(dimethylamino)pyridine; pyridine / CHCl₃

9: NaI / acetone

10: 70.1 percent / SmI₂; N,N-dimethylpropyleneurea / acetonitrile / 0.05 h / -18 °C

11: 1,2-dichloro-ethane / 3 h / 20 °C

12: triflic acid; H₂O / tetrahydrofuran / 3 h

13: 42.8 mg / diisopropylethylamine / dimethylformamide / 2 h

With pyridine; dmap; 1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone; sodium tetrahydroborate; fluorosilicic acid; samarium diiodide; trifluorormethanesulfonic acid; water; sodium ethanolate; triethylamine; N-ethyl-N,N-diisopropylamine; sodium iodide; dichlorobis(tri-O-tolylphosphine)palladium; In tetrahydrofuran; methanol; ethanol; dichloromethane; chloroform; water; 1,2-dichloro-ethane; N,N-dimethyl-formamide; acetone; acetonitrile;

DOI:10.1016/j.tet.2006.12.055

Reference yield:

(5S,6S)-1-benzyl-5-(tert-butyldimethylsilanyloxy)-6-methyl-4-trifluoromethanesulfonyloxy-5,6-dihydro-1H-pyridin-2-one (930579-52-5) → (1S)-2-[(2S)-2-(benzyl-tert-butoxycarbonylamino)propylidene]cyclopentanecarboxylic acid methyl ester (930579-59-2)

Guidance literature:

Multi-step reaction with 10 steps

1: 90.7 percent / Pd[P(o-Tol)3]2Cl₂ / tetrahydrofuran / 1 h / 20 °C

2: 98.7 percent / sodium borohydride / methanol; tetrahydrofuran / 12 h / 0 °C

3: 4-(dimethylamino)pyridine; pyridine / CH₂Cl₂ / 12 h / 20 °C

4: hexafluorosilicic acid / acetonitrile; methanol; H₂O / 3 h / 40 °C

5: 4-(dimethylamino)pyridine; pyridine / CHCl₃

6: NaI / acetone

7: 70.1 percent / SmI₂; N,N-dimethylpropyleneurea / acetonitrile / 0.05 h / -18 °C

8: 1,2-dichloro-ethane / 3 h / 20 °C

9: triflic acid; H₂O / tetrahydrofuran / 3 h

10: 42.8 mg / diisopropylethylamine / dimethylformamide / 2 h

With pyridine; dmap; 1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone; sodium tetrahydroborate; fluorosilicic acid; samarium diiodide; trifluorormethanesulfonic acid; water; N-ethyl-N,N-diisopropylamine; sodium iodide; dichlorobis(tri-O-tolylphosphine)palladium; In tetrahydrofuran; methanol; dichloromethane; chloroform; water; 1,2-dichloro-ethane; N,N-dimethyl-formamide; acetone; acetonitrile;

DOI:10.1016/j.tet.2006.12.055

upstream raw materials:

di-tert-butyl dicarbonate

(5S,6S)-1-benzyl-5-(tert-butyldimethylsilanyloxy)-6-methyl-4-trifluoromethanesulfonyloxy-5,6-dihydro-1H-pyridin-2-one

(2S,3S)-3-(benzylethoxycarbonylacetylamino)-2-(tert-butyldimethylsilanyloxy)butyric acid ethyl ester

(2S,3S)-3-[benzyl(2-nitrobenzenesulfonyl)amino]-2-(tert-butyldimethylsilanyloxy)butyric acid ethyl ester