tert-butyl (2R,3S,4S)-3-(acetyloxy)-4-{[(tert-butoxy)carbonyl]oxy}-2-(4-methoxybenzyl)pyrrolidine-1-carboxylate

Base Information

Chemical Name:tert-butyl (2R,3S,4S)-3-(acetyloxy)-4-{[(tert-butoxy)carbonyl]oxy}-2-(4-methoxybenzyl)pyrrolidine-1-carboxylate
CAS No.:865814-10-4
Molecular Formula:C₂₄H₃₅NO₈
Molecular Weight:465.544
Hs Code.:

Synonyms:tert-butyl (2R,3S,4S)-3-(acetyloxy)-4-{[(tert-butoxy)carbonyl]oxy}-2-(4-methoxybenzyl)pyrrolidine-1-carboxylate

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Chemical Property of tert-butyl (2R,3S,4S)-3-(acetyloxy)-4-{[(tert-butoxy)carbonyl]oxy}-2-(4-methoxybenzyl)pyrrolidine-1-carboxylate

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Technology Process of tert-butyl (2R,3S,4S)-3-(acetyloxy)-4-{[(tert-butoxy)carbonyl]oxy}-2-(4-methoxybenzyl)pyrrolidine-1-carboxylate

There total 7 articles about tert-butyl (2R,3S,4S)-3-(acetyloxy)-4-{[(tert-butoxy)carbonyl]oxy}-2-(4-methoxybenzyl)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:

: tert-butyl (2R,3S,4S)-4-{[(tert-butoxy)carbonyl]oxy}-3-hydroxy-2-(4-methoxybenzyl)pyrrolidine-1-carboxylate

: 108-24-7
acetic anhydride

: 865814-10-4
tert-butyl (2R,3S,4S)-3-(acetyloxy)-4-{[(tert-butoxy)carbonyl]oxy}-2-(4-methoxybenzyl)pyrrolidine-1-carboxylate

Guidance literature:: With dmap; triethylamine; In tetrahydrofuran; dichloromethane; at 0 - 20 ℃; for 12h;
DOI:10.1002/hlca.200590143

Reference yield:

: 865814-07-9
tert-butyl (2R)-2-(4-methoxybenzyl)-3-oxopyrrolidine-1-carboxylate

: 865814-10-4
tert-butyl (2R,3S,4S)-3-(acetyloxy)-4-{[(tert-butoxy)carbonyl]oxy}-2-(4-methoxybenzyl)pyrrolidine-1-carboxylate

Guidance literature:: Multi-step reaction with 5 steps

1.1: BuLi; iPr₂NH / hexane; tetrahydrofuran / 0.33 h / -78 °C

1.2: 68 percent / DMPU / hexane; tetrahydrofuran / -78 - 20 °C

2.1: BH₃*THF / tetrahydrofuran / -30 - 20 °C

2.2: 89 percent / NaOH; aq. H₂O₂ / tetrahydrofuran / 16 h / 20 °C

3.1: 90 percent / DMAP / pyridine / 12 h / 20 °C

4.1: Bu₄NF / tetrahydrofuran / 16 h / 20 °C

5.1: 0.342 g / Et₃N; DMAP / tetrahydrofuran; CH₂Cl₂ / 12 h / 0 - 20 °C

With dmap; n-butyllithium; borane-THF; tetrabutyl ammonium fluoride; triethylamine; diisopropylamine; In tetrahydrofuran; pyridine; hexane; dichloromethane;
DOI:10.1002/hlca.200590143

Reference yield:

: 865814-08-0
tert-butyl (2R)-3-{[(tert-butyl)dimethylsilyl]oxy}-2,5-dihydro-2-(4-methoxybenzyl)-1H-pyrrol-1-carboxylate

: 865814-10-4
tert-butyl (2R,3S,4S)-3-(acetyloxy)-4-{[(tert-butoxy)carbonyl]oxy}-2-(4-methoxybenzyl)pyrrolidine-1-carboxylate

Guidance literature:: Multi-step reaction with 4 steps

1.1: BH₃*THF / tetrahydrofuran / -30 - 20 °C

1.2: 89 percent / NaOH; aq. H₂O₂ / tetrahydrofuran / 16 h / 20 °C

2.1: 90 percent / DMAP / pyridine / 12 h / 20 °C

3.1: Bu₄NF / tetrahydrofuran / 16 h / 20 °C

4.1: 0.342 g / Et₃N; DMAP / tetrahydrofuran; CH₂Cl₂ / 12 h / 0 - 20 °C

With dmap; borane-THF; tetrabutyl ammonium fluoride; triethylamine; In tetrahydrofuran; pyridine; dichloromethane;
DOI:10.1002/hlca.200590143