(3S,4R)-tert-butyl-3-hydroxy-4-(4-fluorophenyl)pyrrolidine-1-carboxylate

Base Information

Chemical Name:(3S,4R)-tert-butyl-3-hydroxy-4-(4-fluorophenyl)pyrrolidine-1-carboxylate
CAS No.:952343-48-5
Molecular Formula:C₁₅H₂₀FNO₃
Molecular Weight:281.327
Hs Code.:

Synonyms:(3S,4R)-tert-butyl-3-hydroxy-4-(4-fluorophenyl)pyrrolidine-1-carboxylate

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Chemical Property of (3S,4R)-tert-butyl-3-hydroxy-4-(4-fluorophenyl)pyrrolidine-1-carboxylate

Chemical Property:

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Technology Process of (3S,4R)-tert-butyl-3-hydroxy-4-(4-fluorophenyl)pyrrolidine-1-carboxylate

There total 4 articles about (3S,4R)-tert-butyl-3-hydroxy-4-(4-fluorophenyl)pyrrolidine-1-carboxylate 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:

: 352-13-6
4-flourophenylmagnesium bromide

: 114214-49-2
rac-tert-butyl (1R,5S)-6-oxa-3-azabicyclo[3.1.0]hexane-3-carboxylate

: 952343-48-5
(3S,4R)-tert-butyl-3-hydroxy-4-(4-fluorophenyl)pyrrolidine-1-carboxylate

: 849674-41-5
(-)-tert-butyl (3S,4R)-3-(4-fluorophenyl)-4-hydroxypyrrolidine-1-carboxylate

Guidance literature:: With copper(l) iodide; In tetrahydrofuran; at 0 ℃;
DOI:10.1016/j.bmcl.2007.06.085

Reference yield:

: (trans)-3-(4-fluorophenyl)-4-hydroxypyrrolidine-1-carboxylic acid tert-butyl ester

: 952343-48-5
(3S,4R)-tert-butyl-3-hydroxy-4-(4-fluorophenyl)pyrrolidine-1-carboxylate

: 849674-41-5
(-)-tert-butyl (3S,4R)-3-(4-fluorophenyl)-4-hydroxypyrrolidine-1-carboxylate

: (-)-tert-butyl (R)-3-(4-fluorophenyl)-4-oxopyrrolidine-1-carboxylate

Guidance literature:: With trichloroisocyanuric acid; (1R,3R,6R,7S,8R)-7-benzyl-3-n-butyl-4-oxa-5-azahomoadamantane; sodium hydrogencarbonate; In dichloromethane; at -40 ℃; for 24h; enantioselective reaction; Inert atmosphere;
DOI:10.1021/ja509766f

Reference yield:

: 73286-70-1
N-(tert-butoxycarbonyl)-3-pyrroline

: 952343-48-5
(3S,4R)-tert-butyl-3-hydroxy-4-(4-fluorophenyl)pyrrolidine-1-carboxylate

: 849674-41-5
(-)-tert-butyl (3S,4R)-3-(4-fluorophenyl)-4-hydroxypyrrolidine-1-carboxylate

: (-)-tert-butyl (R)-3-(4-fluorophenyl)-4-oxopyrrolidine-1-carboxylate

Guidance literature:: Multi-step reaction with 3 steps

1.1: 3-chloro-benzenecarboperoxoic acid / dichloromethane / 12 h / 20 °C / Inert atmosphere

2.1: iodine; magnesium; copper(l) iodide / tetrahydrofuran / 0.25 h / 0 °C / Inert atmosphere

2.2: 0.5 h / 0 °C / Inert atmosphere

3.1: (1R,3R,6R,7S,8R)-7-benzyl-3-n-butyl-4-oxa-5-azahomoadamantane; sodium hydrogencarbonate; trichloroisocyanuric acid / dichloromethane / 24 h / -40 °C / Inert atmosphere

With copper(l) iodide; trichloroisocyanuric acid; (1R,3R,6R,7S,8R)-7-benzyl-3-n-butyl-4-oxa-5-azahomoadamantane; iodine; sodium hydrogencarbonate; magnesium; 3-chloro-benzenecarboperoxoic acid; In tetrahydrofuran; dichloromethane;
DOI:10.1021/ja509766f