benzyl (2R,3S,5S)-2-acetyloxy-5-tert-butyldimethylsilyloxymethyl-3-(monofluoromethyl)pyrrolidine-1-carboxylate

Base Information

Chemical Name:benzyl (2R,3S,5S)-2-acetyloxy-5-tert-butyldimethylsilyloxymethyl-3-(monofluoromethyl)pyrrolidine-1-carboxylate
CAS No.:832133-04-7
Molecular Formula:C₂₂H₃₄FNO₅Si
Molecular Weight:439.6
Hs Code.:

Synonyms:benzyl (2R,3S,5S)-2-acetyloxy-5-tert-butyldimethylsilyloxymethyl-3-(monofluoromethyl)pyrrolidine-1-carboxylate

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Chemical Property of benzyl (2R,3S,5S)-2-acetyloxy-5-tert-butyldimethylsilyloxymethyl-3-(monofluoromethyl)pyrrolidine-1-carboxylate

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Technology Process of benzyl (2R,3S,5S)-2-acetyloxy-5-tert-butyldimethylsilyloxymethyl-3-(monofluoromethyl)pyrrolidine-1-carboxylate

There total 6 articles about benzyl (2R,3S,5S)-2-acetyloxy-5-tert-butyldimethylsilyloxymethyl-3-(monofluoromethyl)pyrrolidine-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: 92.0%

: 832133-02-5
benzyl (2R,3S,5S)-5-tert-butyldimethylsilyloxymethyl-3-monofluoromethyl-2-hydroxypyrrolidine-1-carboxylate

: 108-24-7
acetic anhydride

: 832133-04-7
benzyl (2R,3S,5S)-2-acetyloxy-5-tert-butyldimethylsilyloxymethyl-3-(monofluoromethyl)pyrrolidine-1-carboxylate

Guidance literature:: With pyridine; dmap; In dichloromethane; at 20 ℃;
DOI:10.1016/j.bmc.2004.09.040

Reference yield:

: 832132-91-9
methyl (2S)-N-tert-butoxycarbonyl-4-[(Z)-fluoromethylidene]pyroglutamate

: 832133-04-7
benzyl (2R,3S,5S)-2-acetyloxy-5-tert-butyldimethylsilyloxymethyl-3-(monofluoromethyl)pyrrolidine-1-carboxylate

Guidance literature:: Multi-step reaction with 5 steps

1.1: 84 percent / H₂ / Pd on BaSO₄ / dioxane / 24 h / 20 °C / 760 Torr

2.1: trifluoroacetic acid / CH₂Cl₂ / -78 - 20 °C

2.2: NaBH₄ / methanol / 1.5 h / 0 °C

2.3: 67 percent / DMAP; imidazole / CH₂Cl₂; dimethylformamide / 20 °C

3.1: 93 percent / LHMDS / tetrahydrofuran / 0.17 h / -78 °C

4.1: 81 percent / LiBEt₃H / tetrahydrofuran / 1 h / -78 °C

5.1: 92 percent / DMAP; pyridine / CH₂Cl₂ / 20 °C

With pyridine; dmap; hydrogen; lithium triethylborohydride; trifluoroacetic acid; lithium hexamethyldisilazane; palladium on barium sulfate; In tetrahydrofuran; 1,4-dioxane; dichloromethane;
DOI:10.1016/j.bmc.2004.09.040

Reference yield:

: methyl (2S)-N-tert-butoxycarbonyl-4-difluoromethylpyroglutamate

: 832133-04-7
benzyl (2R,3S,5S)-2-acetyloxy-5-tert-butyldimethylsilyloxymethyl-3-(monofluoromethyl)pyrrolidine-1-carboxylate

Guidance literature:: Multi-step reaction with 6 steps

1.1: 75 percent / Et₃N / tetrahydrofuran / 20 °C

2.1: 84 percent / H₂ / Pd on BaSO₄ / dioxane / 24 h / 20 °C / 760 Torr

3.1: trifluoroacetic acid / CH₂Cl₂ / -78 - 20 °C

3.2: NaBH₄ / methanol / 1.5 h / 0 °C

3.3: 67 percent / DMAP; imidazole / CH₂Cl₂; dimethylformamide / 20 °C

4.1: 93 percent / LHMDS / tetrahydrofuran / 0.17 h / -78 °C

5.1: 81 percent / LiBEt₃H / tetrahydrofuran / 1 h / -78 °C

6.1: 92 percent / DMAP; pyridine / CH₂Cl₂ / 20 °C

With pyridine; dmap; hydrogen; lithium triethylborohydride; triethylamine; trifluoroacetic acid; lithium hexamethyldisilazane; palladium on barium sulfate; In tetrahydrofuran; 1,4-dioxane; dichloromethane;
DOI:10.1016/j.bmc.2004.09.040