(3R,5S)-1-(tert-butoxycarbonyl)-5-methoxymethyl-3-phenylseleno-2-pyrrolidinone

Base Information

Chemical Name:(3R,5S)-1-(tert-butoxycarbonyl)-5-methoxymethyl-3-phenylseleno-2-pyrrolidinone
CAS No.:145221-01-8
Molecular Formula:C₁₇H₂₃NO₄Se
Molecular Weight:384.334
Hs Code.:

Synonyms:(3R,5S)-1-(tert-butoxycarbonyl)-5-methoxymethyl-3-phenylseleno-2-pyrrolidinone

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

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Chemical Property of (3R,5S)-1-(tert-butoxycarbonyl)-5-methoxymethyl-3-phenylseleno-2-pyrrolidinone

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Technology Process of (3R,5S)-1-(tert-butoxycarbonyl)-5-methoxymethyl-3-phenylseleno-2-pyrrolidinone

There total 9 articles about (3R,5S)-1-(tert-butoxycarbonyl)-5-methoxymethyl-3-phenylseleno-2-pyrrolidinone 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: 45.0%

: 186581-53-3,908094-01-9,334-88-3
diazomethane

: 132430-60-5
(3R,5S)-1-(tert-butoxycarbonyl)-5-hydroxymethyl-3-phenylseleno-2-pyrrolidinone

: 145221-01-8
(3R,5S)-1-(tert-butoxycarbonyl)-5-methoxymethyl-3-phenylseleno-2-pyrrolidinone

Guidance literature:: With tetrafluoroboric acid; In dichloromethane; at 0 ℃; for 0.05h;
DOI:10.1248/cpb.40.1925

Reference yield:

: 17342-08-4
(S)-Pyroglutaminol

: 145221-00-7,145221-01-8
(S)-5-Methoxymethyl-2-oxo-3-phenylselanyl-pyrrolidine-1-carboxylic acid tert-butyl ester

Guidance literature:: Multi-step reaction with 5 steps

1: 100 percent / imidazole / dimethylformamide / 12 h / 0 °C

2: 81 percent / Et₃N, 4-dimethylaminopyridine / CH₂Cl₂ / 5 h / Ambient temperature

3: 94 percent / 1 M tetrabutylammonium fluoride / tetrahydrofuran / 0.5 h / Ambient temperature

4: 74 percent / conc. fluoroboric acid / CH₂Cl₂ / 0.05 h / 0 °C

5: 1.) LDA / 1.) THF, hexane, -78 deg C, 40 min, 2.) THF, hexane, -78 deg C, 15 min

With 1H-imidazole; dmap; tetrafluoroboric acid; tetrabutyl ammonium fluoride; triethylamine; lithium diisopropyl amide; In tetrahydrofuran; dichloromethane; N,N-dimethyl-formamide;
DOI:10.1248/cpb.40.1925

Reference yield:

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

: 145221-00-7,145221-01-8
(S)-5-Methoxymethyl-2-oxo-3-phenylselanyl-pyrrolidine-1-carboxylic acid tert-butyl ester

Guidance literature:: Multi-step reaction with 4 steps

1: 81 percent / Et₃N, 4-dimethylaminopyridine / CH₂Cl₂ / 5 h / Ambient temperature

2: 94 percent / 1 M tetrabutylammonium fluoride / tetrahydrofuran / 0.5 h / Ambient temperature

3: 74 percent / conc. fluoroboric acid / CH₂Cl₂ / 0.05 h / 0 °C

4: 1.) LDA / 1.) THF, hexane, -78 deg C, 40 min, 2.) THF, hexane, -78 deg C, 15 min

With dmap; tetrafluoroboric acid; tetrabutyl ammonium fluoride; triethylamine; lithium diisopropyl amide; In tetrahydrofuran; dichloromethane;
DOI:10.1248/cpb.40.1925