(2S)-N-[(tert-butoxy)carbonyl]-1-{{[(tert-butyl)dimethylsilyl]oxy}methyl}-3-(2,4,6-trimethylphenyl)aziridine

Base Information

Chemical Name:(2S)-N-[(tert-butoxy)carbonyl]-1-{{[(tert-butyl)dimethylsilyl]oxy}methyl}-3-(2,4,6-trimethylphenyl)aziridine
CAS No.:287929-79-7
Molecular Formula:C₂₃H₃₉NO₃Si
Molecular Weight:405.653
Hs Code.:

Synonyms:(2S)-N-[(tert-butoxy)carbonyl]-1-{{[(tert-butyl)dimethylsilyl]oxy}methyl}-3-(2,4,6-trimethylphenyl)aziridine

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Chemical Property of (2S)-N-[(tert-butoxy)carbonyl]-1-{{[(tert-butyl)dimethylsilyl]oxy}methyl}-3-(2,4,6-trimethylphenyl)aziridine

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Technology Process of (2S)-N-[(tert-butoxy)carbonyl]-1-{{[(tert-butyl)dimethylsilyl]oxy}methyl}-3-(2,4,6-trimethylphenyl)aziridine

There total 10 articles about (2S)-N-[(tert-butoxy)carbonyl]-1-{{[(tert-butyl)dimethylsilyl]oxy}methyl}-3-(2,4,6-trimethylphenyl)aziridine 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%

: 287929-78-6
(1R,2R)-2-{[(tert-butoxy)carbonyl]amino}-1-{{[(tert-butyl)dimethylsilyl]oxy}methyl}-2-(2,4,6-trimethylphenyl)ethyl methanesulfonate

: 287929-79-7
(2S)-N-[(tert-butoxy)carbonyl]-1-{{[(tert-butyl)dimethylsilyl]oxy}methyl}-3-(2,4,6-trimethylphenyl)aziridine

Guidance literature:: With sodium hydride; In tetrahydrofuran; at 20 ℃; for 3h;
DOI:10.1002/(SICI)1522-2675(20000510)83:5<972::AID-HLCA972>3.0.CO;2-9

Reference yield:

: 487-68-3
mesytaldehyde

: 287929-79-7
(2S)-N-[(tert-butoxy)carbonyl]-1-{{[(tert-butyl)dimethylsilyl]oxy}methyl}-3-(2,4,6-trimethylphenyl)aziridine

Guidance literature:: Multi-step reaction with 8 steps

1: 97 percent / CH₂Cl₂ / 24 h / Heating

2: 86 percent / DIBAL-H / diethyl ether; hexane / 5 h / 20 °C

3: 4 Angstroem mol. sieves; titanium tetraisopropoxide; tert-butyl hydroperoxide / (+)-diisopropyl L-tartrate / CH₂Cl₂; 2,2,4-trimethyl-pentane / 8 h / -30 °C

4: 97 percent / LiClO₄ / acetonitrile / 24 h / 65 °C

5: 68 percent / H₂ / 15 percent Pd(OH)2/C / methanol / 48 h / 20 °C / 760 Torr

6: 91 percent / 1H-imidazole / dimethylformamide / 24 h / 20 °C

7: 82 percent / Et₃N; 4-(dimethylamino)pyridine / CH₂Cl₂ / 5 h / -15 - 20 °C

8: 94 percent / NaH / tetrahydrofuran / 3 h / 20 °C

With 1H-imidazole; titanium(IV) isopropylate; tert.-butylhydroperoxide; dmap; 4 A molecular sieve; hydrogen; lithium perchlorate; sodium hydride; diisobutylaluminium hydride; triethylamine; palladium dihydroxide; L-(+)-diisopropyl tartrate; In tetrahydrofuran; methanol; 2,2,4-trimethylpentane; diethyl ether; hexane; dichloromethane; N,N-dimethyl-formamide; acetonitrile; 1: Condensation / 2: Reduction / 3: Oxidation / 4: Ring cleavage / 5: Hydrogenation / 6: Etherification / 7: Acylation / 8: Elimination;
DOI:10.1002/(SICI)1522-2675(20000510)83:5<972::AID-HLCA972>3.0.CO;2-9

Reference yield:

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

: 287929-79-7
(2S)-N-[(tert-butoxy)carbonyl]-1-{{[(tert-butyl)dimethylsilyl]oxy}methyl}-3-(2,4,6-trimethylphenyl)aziridine

Guidance literature:: Multi-step reaction with 4 steps

1: 62 percent / H₂ / 10 percent Pd/C / ethyl acetate / 1 Torr

2: 91 percent / 1H-imidazole / dimethylformamide / 24 h / 20 °C

3: 82 percent / Et₃N; 4-(dimethylamino)pyridine / CH₂Cl₂ / 5 h / -15 - 20 °C

4: 94 percent / NaH / tetrahydrofuran / 3 h / 20 °C

With 1H-imidazole; dmap; hydrogen; sodium hydride; triethylamine; palladium on activated charcoal; In tetrahydrofuran; dichloromethane; ethyl acetate; N,N-dimethyl-formamide; 1: Reduction / 2: Etherification / 3: Acylation / 4: Elimination;
DOI:10.1002/(SICI)1522-2675(20000510)83:5<972::AID-HLCA972>3.0.CO;2-9