ethyl trans-4-[1-tert-butoxycarbonyl-(3S)-methoxy-(2R)-pyrrolidinylmethoxy]cyclohexanecarboxylate

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Chemical Name:ethyl trans-4-[1-tert-butoxycarbonyl-(3S)-methoxy-(2R)-pyrrolidinylmethoxy]cyclohexanecarboxylate
CAS No.:1416960-80-9
Molecular Formula:C₂₀H₃₅NO₆
Molecular Weight:385.501
Hs Code.:

Synonyms:ethyl trans-4-[1-tert-butoxycarbonyl-(3S)-methoxy-(2R)-pyrrolidinylmethoxy]cyclohexanecarboxylate

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Chemical Property of ethyl trans-4-[1-tert-butoxycarbonyl-(3S)-methoxy-(2R)-pyrrolidinylmethoxy]cyclohexanecarboxylate

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Technology Process of ethyl trans-4-[1-tert-butoxycarbonyl-(3S)-methoxy-(2R)-pyrrolidinylmethoxy]cyclohexanecarboxylate

There total 12 articles about ethyl trans-4-[1-tert-butoxycarbonyl-(3S)-methoxy-(2R)-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: 31.0%

: 1416960-91-2
4-[1-tert-butoxycarbonyl-(3S)-methoxy-(2R)-pyrrolidinylmethoxy]cyclohexanecarboxylic acid

: 75-03-6
ethyl iodide

: 1416960-80-9
ethyl trans-4-[1-tert-butoxycarbonyl-(3S)-methoxy-(2R)-pyrrolidinylmethoxy]cyclohexanecarboxylate

Guidance literature:: With potassium carbonate; In N,N-dimethyl-formamide; at 70 ℃; for 17h;
DOI:10.1016/j.bmc.2012.11.003

Reference yield:

: 99-76-3,156291-94-0
methyl 4-hydroxylbenzoate

: 1416960-80-9
ethyl trans-4-[1-tert-butoxycarbonyl-(3S)-methoxy-(2R)-pyrrolidinylmethoxy]cyclohexanecarboxylate

Guidance literature:: Multi-step reaction with 7 steps

1.1: triphenylphosphine; di-isopropyl azodicarboxylate / tetrahydrofuran / 12 h / Reflux

2.1: palladium 10% on activated carbon; hydrogen / methanol / 20 h

3.1: Rh/Al₂O₃; hydrogen / methanol; acetic acid / 48 h / 10?atm

4.1: dmap / acetonitrile / 20 h / 20 °C

4.2: 24 h / Reflux

5.1: diazomethyl-trimethyl-silane / benzene; hexane / 2 h / 20 °C

6.1: sodium hydroxide / dichloromethane / 96 h / 20 °C

7.1: potassium carbonate / N,N-dimethyl-formamide / 17 h / 70 °C

With dmap; di-isopropyl azodicarboxylate; palladium 10% on activated carbon; Rh/Al₂O₃; hydrogen; potassium carbonate; triphenylphosphine; sodium hydroxide; diazomethyl-trimethyl-silane; In tetrahydrofuran; methanol; hexane; dichloromethane; acetic acid; N,N-dimethyl-formamide; acetonitrile; benzene; 1.1: |Mitsunobu Displacement;
DOI:10.1016/j.bmc.2012.11.003

Reference yield:

: 441717-58-4
1-benzyloxycarbonyl-(3S)-methoxy-(2R)-pyrrolidinemethanol

: 1416960-80-9
ethyl trans-4-[1-tert-butoxycarbonyl-(3S)-methoxy-(2R)-pyrrolidinylmethoxy]cyclohexanecarboxylate

Guidance literature:: Multi-step reaction with 7 steps

1.1: triphenylphosphine; di-isopropyl azodicarboxylate / tetrahydrofuran / 12 h / Reflux

2.1: palladium 10% on activated carbon; hydrogen / methanol / 20 h

3.1: Rh/Al₂O₃; hydrogen / methanol; acetic acid / 48 h / 10?atm

4.1: dmap / acetonitrile / 20 h / 20 °C

4.2: 24 h / Reflux

5.1: diazomethyl-trimethyl-silane / benzene; hexane / 2 h / 20 °C

6.1: sodium hydroxide / dichloromethane / 96 h / 20 °C

7.1: potassium carbonate / N,N-dimethyl-formamide / 17 h / 70 °C

With dmap; di-isopropyl azodicarboxylate; palladium 10% on activated carbon; Rh/Al₂O₃; hydrogen; potassium carbonate; triphenylphosphine; sodium hydroxide; diazomethyl-trimethyl-silane; In tetrahydrofuran; methanol; hexane; dichloromethane; acetic acid; N,N-dimethyl-formamide; acetonitrile; benzene; 1.1: |Mitsunobu Displacement;
DOI:10.1016/j.bmc.2012.11.003