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

Base Information

Chemical Name:(2R,4S)-1-allyloxycarbonyl-4-benzylthio-2-[(4-hydroxymethyl-1-methylpyrazol-5-yl)methyl]pyrrolidine
CAS No.:164162-08-7
Molecular Formula:C₂₁H₂₅N₃O₄S
Molecular Weight:415.513
Hs Code.:

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

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Chemical Property of (2R,4S)-1-allyloxycarbonyl-4-benzylthio-2-[(4-hydroxymethyl-1-methylpyrazol-5-yl)methyl]pyrrolidine

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Technology Process of (2R,4S)-1-allyloxycarbonyl-4-benzylthio-2-[(4-hydroxymethyl-1-methylpyrazol-5-yl)methyl]pyrrolidine

There total 15 articles about (2R,4S)-1-allyloxycarbonyl-4-benzylthio-2-[(4-hydroxymethyl-1-methylpyrazol-5-yl)methyl]pyrrolidine 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:

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

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

Guidance literature:: Multi-step reaction with 14 steps

1: 87.9 percent / n-BuLi / tetrahydrofuran; hexane / 3 h / -70 - 5 °C

2: SOCl₂ / 1 h / -20 °C

3: Et₃N / CH₂Cl₂ / 1 h / -15 - -5 °C

4: 47.36 g / AIBN; n-Bu₃SnH / toluene / 1.75 h / Heating

5: 66 percent / Br₂; Na₂CO₃ / CH₂Cl₂ / 0.5 h / 0 °C

6: 591 mg / n-BuLi / diethyl ether; hexane / 1.5 h / -10 - 20 °C

7: 56 percent / NaBH₄ / tetrahydrofuran; methanol / 1 h / 0 - 5 °C

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

9: 6.98 g / aq. NaOH / tetrahydrofuran / 0.17 h / 0 - 5 °C / pH 8.5 - 10

10: Et₃N / ethyl acetate / 1 h / 0 °C

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

12: 7.33 g / Et₃N / ethyl acetate / 1 h / 20 °C

13: 4.32 g / NaOMe / methanol / 0.25 h / 0 °C

14: 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

Reference yield:

: 164162-01-0
(2R,4R)-1-benzyl-4-tert-butyldimethylsilyloxy-2-[(1-methylpyrazol-5-yl)methyl]pyrrolidine

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

Guidance literature:: Multi-step reaction with 10 steps

1: 66 percent / Br₂; Na₂CO₃ / CH₂Cl₂ / 0.5 h / 0 °C

2: 591 mg / n-BuLi / diethyl ether; hexane / 1.5 h / -10 - 20 °C

3: 56 percent / NaBH₄ / tetrahydrofuran; methanol / 1 h / 0 - 5 °C

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

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

6: Et₃N / ethyl acetate / 1 h / 0 °C

7: aq. HCl / methanol / 1.5 h / 20 °C

8: 7.33 g / Et₃N / ethyl acetate / 1 h / 20 °C

9: 4.32 g / NaOMe / methanol / 0.25 h / 0 °C

10: 5.38 g / t-BuOK / dimethylformamide / 3 h / 85 - 90 °C

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

Reference yield:

: 164162-02-1
(2R,4R)-1-benzyl-2-[(4-bromo-1-methylpyrazol-5-yl)methyl]-4-tert-butyldimethylsilyloxypyrrolidine

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

Guidance literature:: Multi-step reaction with 9 steps

1: 591 mg / n-BuLi / diethyl ether; hexane / 1.5 h / -10 - 20 °C

2: 56 percent / NaBH₄ / tetrahydrofuran; methanol / 1 h / 0 - 5 °C

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

4: 6.98 g / aq. NaOH / tetrahydrofuran / 0.17 h / 0 - 5 °C / pH 8.5 - 10

5: Et₃N / ethyl acetate / 1 h / 0 °C

6: aq. HCl / methanol / 1.5 h / 20 °C

7: 7.33 g / Et₃N / ethyl acetate / 1 h / 20 °C

8: 4.32 g / NaOMe / methanol / 0.25 h / 0 °C

9: 5.38 g / t-BuOK / dimethylformamide / 3 h / 85 - 90 °C

With hydrogenchloride; sodium hydroxide; sodium tetrahydroborate; n-butyllithium; potassium tert-butylate; ammonium formate; sodium methylate; triethylamine; palladium on activated charcoal; In tetrahydrofuran; methanol; diethyl ether; hexane; ethyl acetate; N,N-dimethyl-formamide;
DOI:10.1016/S0968-0896(00)00314-X