methyl 4-[1-tert-butoxycarbonyl-(5R)-methoxymethyl-(2S)-pyrrolidinylmethoxy]cyclohexanecarboxylate

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Chemical Name:methyl 4-[1-tert-butoxycarbonyl-(5R)-methoxymethyl-(2S)-pyrrolidinylmethoxy]cyclohexanecarboxylate
CAS No.:441769-35-3
Molecular Formula:C₂₀H₃₅NO₆
Molecular Weight:385.501
Hs Code.:

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

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

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

There total 4 articles about methyl 4-[1-tert-butoxycarbonyl-(5R)-methoxymethyl-(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:

: 24424-99-5
di-tert-butyl dicarbonate

: 1416987-11-5
methyl 4-[(5R)-methoxymethyl-(2S)-pyrrolidinylmethoxy]cyclohexanecarboxylate TFA salt

: 441769-35-3
methyl 4-[1-tert-butoxycarbonyl-(5R)-methoxymethyl-(2S)-pyrrolidinylmethoxy]cyclohexanecarboxylate

Guidance literature:: With sodium hydrogencarbonate; In 1,4-dioxane; water; at 20 ℃; for 2h;
DOI:10.1016/j.bmc.2012.11.003

Reference yield:

: 441717-46-0
(2S)-Benzyloxymethyl-1-tert-butoxycarbonyl-(5R)-methoxymethylpyrrolidine

: 441769-35-3
methyl 4-[1-tert-butoxycarbonyl-(5R)-methoxymethyl-(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 / tetrahydrofuran / 10 h / Reflux

3: trifluoroacetic acid / dichloromethane / 17 h / 20 °C

4: Rh/Al₂O₃; hydrogen / methanol / 24 h / 7600.51 Torr

5: sodium hydrogencarbonate / 1,4-dioxane; water / 2 h / 20 °C

With di-isopropyl azodicarboxylate; palladium 10% on activated carbon; Rh/Al₂O₃; hydrogen; sodium hydrogencarbonate; triphenylphosphine; trifluoroacetic acid; In tetrahydrofuran; 1,4-dioxane; methanol; dichloromethane; water; 2: |Mitsunobu Displacement;
DOI:10.1016/j.bmc.2012.11.003

Reference yield:

: 152612-42-5
(2S,5R)-1-tert-butoxycarbonyl-5-hydroxymethyl-2-benzyloxymethyl pyrrolidine

: 441769-35-3
methyl 4-[1-tert-butoxycarbonyl-(5R)-methoxymethyl-(2S)-pyrrolidinylmethoxy]cyclohexanecarboxylate

Guidance literature:: Multi-step reaction with 6 steps

1: sodium hydride / N,N-dimethyl-formamide / 48 h / 20 °C

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

3: triphenylphosphine; di-isopropyl azodicarboxylate / tetrahydrofuran / 10 h / Reflux

4: trifluoroacetic acid / dichloromethane / 17 h / 20 °C

5: Rh/Al₂O₃; hydrogen / methanol / 24 h / 7600.51 Torr

6: sodium hydrogencarbonate / 1,4-dioxane; water / 2 h / 20 °C

With di-isopropyl azodicarboxylate; palladium 10% on activated carbon; Rh/Al₂O₃; hydrogen; sodium hydride; sodium hydrogencarbonate; triphenylphosphine; trifluoroacetic acid; In tetrahydrofuran; 1,4-dioxane; methanol; dichloromethane; water; N,N-dimethyl-formamide; 3: |Mitsunobu Displacement;
DOI:10.1016/j.bmc.2012.11.003