methyl trans-4-[1-tert-butoxycarbonyl-(5S)-fluoromethyl-(2S)-pyrrolidinylmethoxy]cyclohexanecarboxylate

Base Information

Chemical Name:methyl trans-4-[1-tert-butoxycarbonyl-(5S)-fluoromethyl-(2S)-pyrrolidinylmethoxy]cyclohexanecarboxylate
CAS No.:1416961-13-1
Molecular Formula:C₁₉H₃₂FNO₅
Molecular Weight:373.465
Hs Code.:

Synonyms:methyl trans-4-[1-tert-butoxycarbonyl-(5S)-fluoromethyl-(2S)-pyrrolidinylmethoxy]cyclohexanecarboxylate

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Chemical Property of methyl trans-4-[1-tert-butoxycarbonyl-(5S)-fluoromethyl-(2S)-pyrrolidinylmethoxy]cyclohexanecarboxylate

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Technology Process of methyl trans-4-[1-tert-butoxycarbonyl-(5S)-fluoromethyl-(2S)-pyrrolidinylmethoxy]cyclohexanecarboxylate

There total 5 articles about methyl trans-4-[1-tert-butoxycarbonyl-(5S)-fluoromethyl-(2S)-pyrrolidinylmethoxy]cyclohexanecarboxylate 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:

: 67-56-1
methanol

: C₁₈H₃₀FNO₅

: 1416961-13-1
methyl trans-4-[1-tert-butoxycarbonyl-(5S)-fluoromethyl-(2S)-pyrrolidinylmethoxy]cyclohexanecarboxylate

Guidance literature:: With diazomethyl-trimethyl-silane; In hexane; benzene; at 20 ℃; for 1h;
DOI:10.1016/j.bmc.2012.11.003

Reference yield:

: 138528-06-0
(2S,5S)-5-benzyloxymethyl-1-tert-butoxycarbonyl-2-hydroxymethylpyrrolidine

: 1416961-13-1
methyl trans-4-[1-tert-butoxycarbonyl-(5S)-fluoromethyl-(2S)-pyrrolidinylmethoxy]cyclohexanecarboxylate

Guidance literature:: Multi-step reaction with 7 steps

1: triethylamine / dichloromethane / 1 h / 0 °C

2: tetrabutyl ammonium fluoride / tetrahydrofuran / 8 h / Reflux

3: palladium 10% on activated carbon; hydrogen / methanol / 15 h

4: triphenylphosphine; di-isopropyl azodicarboxylate / 2 h / 60 °C

5: Rh/Al₂O₃; hydrogen / acetic acid; ethanol / 2.5 h / 20 °C / 8?atm

6: sodium methylate / methanol / Reflux

7: diazomethyl-trimethyl-silane / benzene; hexane / 1 h / 20 °C

With di-isopropyl azodicarboxylate; palladium 10% on activated carbon; Rh/Al₂O₃; tetrabutyl ammonium fluoride; hydrogen; sodium methylate; triethylamine; triphenylphosphine; diazomethyl-trimethyl-silane; In tetrahydrofuran; methanol; ethanol; hexane; dichloromethane; acetic acid; benzene; 4: |Mitsunobu Displacement;
DOI:10.1016/j.bmc.2012.11.003

Reference yield:

: 1416961-09-5
(2S)-benzyloxymethyl-1-tert-butoxycarobnyl-(5S)-fluoromethylpyrrolidine

: 1416961-13-1
methyl trans-4-[1-tert-butoxycarbonyl-(5S)-fluoromethyl-(2S)-pyrrolidinylmethoxy]cyclohexanecarboxylate

Guidance literature:: Multi-step reaction with 5 steps

1: palladium 10% on activated carbon; hydrogen / methanol / 15 h

2: triphenylphosphine; di-isopropyl azodicarboxylate / 2 h / 60 °C

3: Rh/Al₂O₃; hydrogen / acetic acid; ethanol / 2.5 h / 20 °C / 8?atm

4: sodium methylate / methanol / Reflux

5: diazomethyl-trimethyl-silane / benzene; hexane / 1 h / 20 °C

With di-isopropyl azodicarboxylate; palladium 10% on activated carbon; Rh/Al₂O₃; hydrogen; sodium methylate; triphenylphosphine; diazomethyl-trimethyl-silane; In methanol; ethanol; hexane; acetic acid; benzene; 2: |Mitsunobu Displacement;
DOI:10.1016/j.bmc.2012.11.003