ethyl (4S,5R)-4-[2-(benzyloxy)ethyl]-4,5-dihydro-5-(hydroxymethyl)pyrazole-1-carboxylate

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Chemical Name:ethyl (4S,5R)-4-[2-(benzyloxy)ethyl]-4,5-dihydro-5-(hydroxymethyl)pyrazole-1-carboxylate
CAS No.:198268-22-3
Molecular Formula:C₁₆H₂₂N₂O₄
Molecular Weight:306.362
Hs Code.:

Synonyms:ethyl (4S,5R)-4-[2-(benzyloxy)ethyl]-4,5-dihydro-5-(hydroxymethyl)pyrazole-1-carboxylate

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Chemical Property of ethyl (4S,5R)-4-[2-(benzyloxy)ethyl]-4,5-dihydro-5-(hydroxymethyl)pyrazole-1-carboxylate

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Technology Process of ethyl (4S,5R)-4-[2-(benzyloxy)ethyl]-4,5-dihydro-5-(hydroxymethyl)pyrazole-1-carboxylate

There total 5 articles about ethyl (4S,5R)-4-[2-(benzyloxy)ethyl]-4,5-dihydro-5-(hydroxymethyl)pyrazole-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: 91.0%

: 198268-11-0
ethyl (4R,5R)-4-[2-(benzyloxy)ethyl]-5-{1-[(S)-10,10-dimethyl-3,3-dioxo-3λ⁶-thia-4-azatricyclo[5.2.1.0^1,5]dec-4-yl]-carbonyl}-4,5-dihydropyrazole-1-carboxylate

: 198268-22-3
ethyl (4S,5R)-4-[2-(benzyloxy)ethyl]-4,5-dihydro-5-(hydroxymethyl)pyrazole-1-carboxylate

Guidance literature:: With lithium aluminium tetrahydride;
DOI:10.1021/jo971571l

Reference yield:

: 198268-10-9
(S)-4-[(E)-5-(benzyloxy)pent-2-enoyl]-10,10-dimethyl-3λ⁶-thia-4-azatricyclo[5.2.1.0^1,5]decane-3,3-dione

: 198268-22-3
ethyl (4S,5R)-4-[2-(benzyloxy)ethyl]-4,5-dihydro-5-(hydroxymethyl)pyrazole-1-carboxylate

Guidance literature:: Multi-step reaction with 2 steps

1.1: mol. sieves / hexane; CH₂Cl₂ / 90 h / 23 °C

1.2: 71 percent / AgOTf / CH₂Cl₂ / 1.5 h / 0 °C

2.1: 91 percent / LiAlH₄ / tetrahydrofuran / 2 h / -78 °C

With lithium aluminium tetrahydride; molecular sieve; In tetrahydrofuran; hexane; dichloromethane; 1.1: Cycloaddition / 1.2: Isomerization / 2.1: Reduction;
DOI:10.1002/1522-2675(20000809)83:8<2007::AID-HLCA2007>3.0.CO;2-5

Reference yield:

: 128217-54-9
5-benzyloxy-2-(E)-pentenocarboxylic acid

: 198268-22-3
ethyl (4S,5R)-4-[2-(benzyloxy)ethyl]-4,5-dihydro-5-(hydroxymethyl)pyrazole-1-carboxylate

Guidance literature:: Multi-step reaction with 4 steps

1.1: oxalyl chloride; DMF / CH₂Cl₂ / 3 h / 0 - 23 °C

2.1: NaH / toluene / 2 h / 23 °C

2.2: 87 percent / toluene / 2 h / 23 °C

3.1: mol. sieves / hexane; CH₂Cl₂ / 90 h / 23 °C

3.2: 71 percent / AgOTf / CH₂Cl₂ / 1.5 h / 0 °C

4.1: 91 percent / LiAlH₄ / tetrahydrofuran / 2 h / -78 °C

With lithium aluminium tetrahydride; molecular sieve; oxalyl dichloride; sodium hydride; N,N-dimethyl-formamide; In tetrahydrofuran; hexane; dichloromethane; toluene; 1.1: Substitution / 2.1: deprotonation / 2.2: Acylation / 3.1: Cycloaddition / 3.2: Isomerization / 4.1: Reduction;
DOI:10.1002/1522-2675(20000809)83:8<2007::AID-HLCA2007>3.0.CO;2-5