(2S,4R)-1-benzyloxycarbonyl-2-(2-fluoroethyloxymethyl)-4-methanesulfonyloxypyrrolidine

Base Information

Chemical Name:(2S,4R)-1-benzyloxycarbonyl-2-(2-fluoroethyloxymethyl)-4-methanesulfonyloxypyrrolidine
CAS No.:127768-05-2
Molecular Formula:C₁₆H₂₂FNO₆S
Molecular Weight:375.418
Hs Code.:

Synonyms:(2S,4R)-1-benzyloxycarbonyl-2-(2-fluoroethyloxymethyl)-4-methanesulfonyloxypyrrolidine

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Chemical Property of (2S,4R)-1-benzyloxycarbonyl-2-(2-fluoroethyloxymethyl)-4-methanesulfonyloxypyrrolidine

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Technology Process of (2S,4R)-1-benzyloxycarbonyl-2-(2-fluoroethyloxymethyl)-4-methanesulfonyloxypyrrolidine

There total 7 articles about (2S,4R)-1-benzyloxycarbonyl-2-(2-fluoroethyloxymethyl)-4-methanesulfonyloxypyrrolidine 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: 74.0%

: 127768-04-1
(2S,4R)-1-benzyloxycarbonyl-2-(2-hydroxyethyloxymethyl)-4-methanesulfonyloxypyrrolidine

: 127768-05-2
(2S,4R)-1-benzyloxycarbonyl-2-(2-fluoroethyloxymethyl)-4-methanesulfonyloxypyrrolidine

Guidance literature:: With hexafluoropropene-diethylamine adduct; In dichloromethane; at 30 - 35 ℃; for 21h;
DOI:10.1016/S0968-0896(97)00142-9

Reference yield:

: 64187-48-0
methyl (2S,4R)-1-benzyloxycarbonyl-4-hydroxypyrrolidine-2-carboxylate

: 127768-05-2
(2S,4R)-1-benzyloxycarbonyl-2-(2-fluoroethyloxymethyl)-4-methanesulfonyloxypyrrolidine

Guidance literature:: Multi-step reaction with 6 steps

1: Et₃N / ethyl acetate / 0.5 h / 0 - 5 °C

2: NaBH₄ / tetrahydrofuran; ethanol / 2 h / 25 - 30 °C

3: t-BuOK / tetrahydrofuran / 1 h / -10 - -5 °C

4: 2N aq. NaOH / tetrahydrofuran / 20 - 25 °C

5: 86 percent / NaBH₄, BF₃*Et₂O / tetrahydrofuran / 1.5 h / -10 - 10 °C

6: 74 percent / Et₂NCF₂CFHCF₃ / CH₂Cl₂ / 21 h / 30 - 35 °C

With sodium hydroxide; sodium tetrahydroborate; hexafluoropropene-diethylamine adduct; boron trifluoride diethyl etherate; potassium tert-butylate; triethylamine; In tetrahydrofuran; ethanol; dichloromethane; ethyl acetate;
DOI:10.1016/S0968-0896(97)00142-9

Reference yield:

: 117811-78-6
methyl (2S,4R)-1-benzyloxycarbonyl-4-methanesulfonyloxypyrrolidine-2-carboxylate

: 127768-05-2
(2S,4R)-1-benzyloxycarbonyl-2-(2-fluoroethyloxymethyl)-4-methanesulfonyloxypyrrolidine

Guidance literature:: Multi-step reaction with 5 steps

1: NaBH₄ / tetrahydrofuran; ethanol / 2 h / 25 - 30 °C

2: t-BuOK / tetrahydrofuran / 1 h / -10 - -5 °C

3: 2N aq. NaOH / tetrahydrofuran / 20 - 25 °C

4: 86 percent / NaBH₄, BF₃*Et₂O / tetrahydrofuran / 1.5 h / -10 - 10 °C

5: 74 percent / Et₂NCF₂CFHCF₃ / CH₂Cl₂ / 21 h / 30 - 35 °C

With sodium hydroxide; sodium tetrahydroborate; hexafluoropropene-diethylamine adduct; boron trifluoride diethyl etherate; potassium tert-butylate; In tetrahydrofuran; ethanol; dichloromethane;
DOI:10.1016/S0968-0896(97)00142-9