(RS)-[(2S,4R)-1-benzyl-4-tert-butyldimethylsilyloxypyrrolidin-2-yl]-(1-methylpyrazol-5-yl)methanol

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Chemical Name:(RS)-[(2S,4R)-1-benzyl-4-tert-butyldimethylsilyloxypyrrolidin-2-yl]-(1-methylpyrazol-5-yl)methanol
CAS No.:351529-73-2
Molecular Formula:C₂₂H₃₅N₃O₂Si
Molecular Weight:401.624
Hs Code.:

Synonyms:(RS)-[(2S,4R)-1-benzyl-4-tert-butyldimethylsilyloxypyrrolidin-2-yl]-(1-methylpyrazol-5-yl)methanol

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Chemical Property of (RS)-[(2S,4R)-1-benzyl-4-tert-butyldimethylsilyloxypyrrolidin-2-yl]-(1-methylpyrazol-5-yl)methanol

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Technology Process of (RS)-[(2S,4R)-1-benzyl-4-tert-butyldimethylsilyloxypyrrolidin-2-yl]-(1-methylpyrazol-5-yl)methanol

There total 1 articles about (RS)-[(2S,4R)-1-benzyl-4-tert-butyldimethylsilyloxypyrrolidin-2-yl]-(1-methylpyrazol-5-yl)methanol 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: 88.0%

: 930-36-9
1-methyl-1H-pyrazole

: 156440-98-1
(2S,4R)-N-benzyl-4-(tert-butyldimethylsilyloxy)pyrrolidine-2-carbaldehyde

: 351529-73-2
(RS)-[(2S,4R)-1-benzyl-4-tert-butyldimethylsilyloxypyrrolidin-2-yl]-(1-methylpyrazol-5-yl)methanol

Guidance literature:: at -78 - 20 ℃;
DOI:10.1016/S0960-894X(97)00230-8

Reference yield:

: 351529-73-2
(RS)-[(2S,4R)-1-benzyl-4-tert-butyldimethylsilyloxypyrrolidin-2-yl]-(1-methylpyrazol-5-yl)methanol

: 156441-99-5
(2R,4S)-1-Allyloxycarbonyl-4-benzoylthio-2-(1-methylpyrazol-5-ylmethyl)-pyrrolidine

Guidance literature:: Multi-step reaction with 6 steps

1: HCO₂NH₄ / Pd/C / methanol / 0.67 h / Heating

2: 103.6 g / aq. NaOH / tetrahydrofuran / 0.17 h / 0 - 5 °C / pH 8.5 - 10

3: pyridine / CH₂Cl₂ / 3.5 h / 0 - 20 °C

4: 55.5 g / AIBN; n-Bu₃SnH / toluene / 3.5 h / Heating

5: aq. HCl / methanol / 1.75 h / 0 - 20 °C

6: PPh₃; DEAD / tetrahydrofuran / 2 h / 20 °C

With pyridine; hydrogenchloride; sodium hydroxide; 2,2'-azobis(isobutyronitrile); tri-n-butyl-tin hydride; ammonium formate; triphenylphosphine; diethylazodicarboxylate; palladium on activated charcoal; In tetrahydrofuran; methanol; dichloromethane; toluene; 6: Mitsunobu reaction;
DOI:10.1016/S0968-0896(00)00314-X

Reference yield:

: 351529-73-2
(RS)-[(2S,4R)-1-benzyl-4-tert-butyldimethylsilyloxypyrrolidin-2-yl]-(1-methylpyrazol-5-yl)methanol

: 164162-08-7
(2R,4S)-1-allyloxycarbonyl-4-benzylthio-2-[(4-hydroxymethyl-1-methylpyrazol-5-yl)methyl]pyrrolidine

Guidance literature:: Multi-step reaction with 13 steps

1: SOCl₂ / 1 h / -20 °C

2: Et₃N / CH₂Cl₂ / 1 h / -15 - -5 °C

3: 47.36 g / AIBN; n-Bu₃SnH / toluene / 1.75 h / Heating

4: 66 percent / Br₂; Na₂CO₃ / CH₂Cl₂ / 0.5 h / 0 °C

5: 591 mg / n-BuLi / diethyl ether; hexane / 1.5 h / -10 - 20 °C

6: 56 percent / NaBH₄ / tetrahydrofuran; methanol / 1 h / 0 - 5 °C

7: HCO₂NH₄ / Pd/C / methanol / 0.67 h / Heating

8: 6.98 g / aq. NaOH / tetrahydrofuran / 0.17 h / 0 - 5 °C / pH 8.5 - 10

9: Et₃N / ethyl acetate / 1 h / 0 °C

10: aq. HCl / methanol / 1.5 h / 20 °C

11: 7.33 g / Et₃N / ethyl acetate / 1 h / 20 °C

12: 4.32 g / NaOMe / methanol / 0.25 h / 0 °C

13: 5.38 g / t-BuOK / dimethylformamide / 3 h / 85 - 90 °C

With hydrogenchloride; sodium hydroxide; sodium tetrahydroborate; n-butyllithium; thionyl chloride; 2,2'-azobis(isobutyronitrile); potassium tert-butylate; bromine; tri-n-butyl-tin hydride; ammonium formate; sodium methylate; sodium carbonate; triethylamine; palladium on activated charcoal; In tetrahydrofuran; methanol; diethyl ether; hexane; dichloromethane; ethyl acetate; N,N-dimethyl-formamide; toluene;
DOI:10.1016/S0968-0896(00)00314-X