tert-butyl 2-(((S)-1,3-bis(benzyloxy)-1-oxopropan-2-yl)carbamoyl)-2-(hydroxymethyl)pyrrolidine-1-carboxylate

Base Information

Chemical Name:tert-butyl 2-(((S)-1,3-bis(benzyloxy)-1-oxopropan-2-yl)carbamoyl)-2-(hydroxymethyl)pyrrolidine-1-carboxylate
CAS No.:1621435-32-2
Molecular Formula:C₂₈H₃₆N₂O₇
Molecular Weight:512.603
Hs Code.:

Synonyms:tert-butyl 2-(((S)-1,3-bis(benzyloxy)-1-oxopropan-2-yl)carbamoyl)-2-(hydroxymethyl)pyrrolidine-1-carboxylate

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Chemical Property of tert-butyl 2-(((S)-1,3-bis(benzyloxy)-1-oxopropan-2-yl)carbamoyl)-2-(hydroxymethyl)pyrrolidine-1-carboxylate

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Technology Process of tert-butyl 2-(((S)-1,3-bis(benzyloxy)-1-oxopropan-2-yl)carbamoyl)-2-(hydroxymethyl)pyrrolidine-1-carboxylate

There total 5 articles about tert-butyl 2-(((S)-1,3-bis(benzyloxy)-1-oxopropan-2-yl)carbamoyl)-2-(hydroxymethyl)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: 76.5%

: 1621435-12-8
1-(tert-butoxycarbonyl)-2-(hydroxymethyl)pyrrolidine-2-carboxylic acid

: 1279028-21-5
(S)-benzyl 2-amino-3-(benzyloxy)propanoate hydrochloride

: 1621435-32-2
tert-butyl 2-(((S)-1,3-bis(benzyloxy)-1-oxopropan-2-yl)carbamoyl)-2-(hydroxymethyl)pyrrolidine-1-carboxylate

Guidance literature:: With N-ethyl-N,N-diisopropylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate; In dichloromethane; at 0 - 20 ℃; for 12h;

Reference yield:

: 147-85-3,25191-13-3,37159-97-0,4305-67-3,4607-28-7
L-proline

: 1621435-32-2
tert-butyl 2-(((S)-1,3-bis(benzyloxy)-1-oxopropan-2-yl)carbamoyl)-2-(hydroxymethyl)pyrrolidine-1-carboxylate

Guidance literature:: Multi-step reaction with 6 steps

1.1: thionyl chloride / 0 °C / Reflux

2.1: triethylamine / dichloromethane / 16 h / 0 - 20 °C

3.1: lithium hexamethyldisilazane / tetrahydrofuran / 1 h / -78 °C

3.2: 2 h / -78 - -20 °C

4.1: sodium hydroxide / water; methanol / 4 h / Reflux

5.1: hydrogen; palladium 10% on activated carbon / methanol / 24 h / 20 °C

6.1: N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate; N-ethyl-N,N-diisopropylamine / dichloromethane / 12 h / 0 - 20 °C

With thionyl chloride; palladium 10% on activated carbon; hydrogen; triethylamine; N-ethyl-N,N-diisopropylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate; sodium hydroxide; lithium hexamethyldisilazane; In tetrahydrofuran; methanol; dichloromethane; water;

Reference yield:

: 59936-29-7
(S)-N-(tert-butoxycarbonyl)proline methyl ester

: 1621435-32-2
tert-butyl 2-(((S)-1,3-bis(benzyloxy)-1-oxopropan-2-yl)carbamoyl)-2-(hydroxymethyl)pyrrolidine-1-carboxylate

Guidance literature:: Multi-step reaction with 4 steps

1.1: lithium hexamethyldisilazane / tetrahydrofuran / 1 h / -78 °C

1.2: 2 h / -78 - -20 °C

2.1: sodium hydroxide / water; methanol / 4 h / Reflux

3.1: hydrogen; palladium 10% on activated carbon / methanol / 24 h / 20 °C

4.1: N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate; N-ethyl-N,N-diisopropylamine / dichloromethane / 12 h / 0 - 20 °C

With palladium 10% on activated carbon; hydrogen; N-ethyl-N,N-diisopropylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate; sodium hydroxide; lithium hexamethyldisilazane; In tetrahydrofuran; methanol; dichloromethane; water;