(2R,4S)-1-allyloxycarbonyl-4-benzoylthio-2-[2-(1,2, 4-triazol-1-yl)ethyl]pyrrolidine

Base Information

Chemical Name:(2R,4S)-1-allyloxycarbonyl-4-benzoylthio-2-[2-(1,2, 4-triazol-1-yl)ethyl]pyrrolidine
CAS No.:156442-44-3
Molecular Formula:C₁₉H₂₂N₄O₃S
Molecular Weight:386.475
Hs Code.:

Synonyms:(2R,4S)-1-allyloxycarbonyl-4-benzoylthio-2-[2-(1,2, 4-triazol-1-yl)ethyl]pyrrolidine

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Chemical Property of (2R,4S)-1-allyloxycarbonyl-4-benzoylthio-2-[2-(1,2, 4-triazol-1-yl)ethyl]pyrrolidine

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Technology Process of (2R,4S)-1-allyloxycarbonyl-4-benzoylthio-2-[2-(1,2, 4-triazol-1-yl)ethyl]pyrrolidine

There total 10 articles about (2R,4S)-1-allyloxycarbonyl-4-benzoylthio-2-[2-(1,2, 4-triazol-1-yl)ethyl]pyrrolidine 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%

: 98-91-9
thiobenzoic acid

: 156442-43-2
(2R,4R)-1-allyloxycarbonyl-4-hydroxy-2-[2-(1,2,4-triazol-1-yl)ethyl]pyrrolidine

: 156442-44-3
(2R,4S)-1-allyloxycarbonyl-4-benzoylthio-2-[2-(1,2, 4-triazol-1-yl)ethyl]pyrrolidine

Guidance literature:: With triphenylphosphine; diethylazodicarboxylate; In tetrahydrofuran; at 0 ℃;
DOI:10.1016/S0968-0896(99)00085-1

Reference yield:

: 98-91-9
thiobenzoic acid

: 156442-43-2
(2R,4R)-1-allyloxycarbonyl-4-hydroxy-2-[2-(1,2,4-triazol-1-yl)ethyl]pyrrolidine

: 1972-28-7,218603-74-8
diethylazodicarboxylate

: 156442-44-3
(2R,4S)-1-allyloxycarbonyl-4-benzoylthio-2-[2-(1,2, 4-triazol-1-yl)ethyl]pyrrolidine

Guidance literature:: With triphenylphosphine; In tetrahydrofuran;

Reference yield:

: 154343-02-9
(2S,4R)-4-{[1-(tert-butyl)-1,1-dimethylsilyl]-oxy}-1-benzyl-2-hydroxy-methyl-pyrrolidin

: 156442-44-3
(2R,4S)-1-allyloxycarbonyl-4-benzoylthio-2-[2-(1,2, 4-triazol-1-yl)ethyl]pyrrolidine

Guidance literature:: Multi-step reaction with 9 steps

1.1: oxalyl chloride; DMSO; Et₃N / CH₂Cl₂ / 1.17 h / -50 - 20 °C

2.1: t-BuOK / tetrahydrofuran / 2 h / 20 °C

2.2: 50.4 percent / tetrahydrofuran / 1 h / 0 - 5 °C

3.1: 9-borabicyclo[3.3.1]nonane / tetrahydrofuran / 4 h / 20 °C

3.2: 82.3 percent / NaBO₃*4H₂O / tetrahydrofuran; H₂O / 12 h / 20 °C

4.1: hydrogen / Pd/C / cyclopentane / 3 h / 20 °C / 760 Torr

5.1: 18.52 g / NaOH / tetrahydrofuran; H₂O / 0.5 h / 0 - 10 °C / pH 8 - 10

6.1: 75.6 percent / Et₃N / CH₂Cl₂ / 0 °C

7.1: NaH / dimethylformamide / 80 - 90 °C

8.1: conc. HCl / methanol / 0 - 5 °C

9.1: 94 percent / Ph₃P; diethyl azodicarboxylate / tetrahydrofuran / 0 °C

With hydrogenchloride; sodium hydroxide; oxalyl dichloride; potassium tert-butylate; hydrogen; sodium hydride; dimethyl sulfoxide; triethylamine; 9-bora-bicyclo[3.3.1]nonane; triphenylphosphine; diethylazodicarboxylate; palladium on activated charcoal; In tetrahydrofuran; methanol; dichloromethane; Cyclopentane; water; N,N-dimethyl-formamide; 1.1: Swern oxidation / 2.1: Dehydrochlorination / 2.2: Wittig reaction / 3.1: hydroboration / 3.2: Oxidation / 4.1: Hydrogenolysis / 5.1: Acylation / 6.1: mesylation / 7.1: Alkylation / 8.1: Hydrolysis / 9.1: Esterification;
DOI:10.1016/S0968-0896(99)00085-1