1-tert-butyl 3-methyl (3S,5R)-5-(benzyloxycarbonylamino)piperidine-1,3-dicarboxylate

Base Information

Chemical Name:1-tert-butyl 3-methyl (3S,5R)-5-(benzyloxycarbonylamino)piperidine-1,3-dicarboxylate
CAS No.:1448902-04-2
Molecular Formula:C₂₀H₂₈N₂O₆
Molecular Weight:392.452
Hs Code.:

Synonyms:1-tert-butyl 3-methyl (3S,5R)-5-(benzyloxycarbonylamino)piperidine-1,3-dicarboxylate

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Chemical Property of 1-tert-butyl 3-methyl (3S,5R)-5-(benzyloxycarbonylamino)piperidine-1,3-dicarboxylate

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Technology Process of 1-tert-butyl 3-methyl (3S,5R)-5-(benzyloxycarbonylamino)piperidine-1,3-dicarboxylate

There total 7 articles about 1-tert-butyl 3-methyl (3S,5R)-5-(benzyloxycarbonylamino)piperidine-1,3-dicarboxylate 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: 96.0%

: 534572-20-8
(3S,5R)-1-(tert-butoxycarbonyl)-3-(methoxycarbonyl)piperidine-5-carboxylic acid

: 1448902-04-2
1-tert-butyl 3-methyl (3S,5R)-5-(benzyloxycarbonylamino)piperidine-1,3-dicarboxylate

Guidance literature:: (3S,5R)-1-(tert-butoxycarbonyl)-3-(methoxycarbonyl)piperidine-5-carboxylic acid; With diphenylphosphoranyl azide; triethylamine; In toluene; at 90 ℃; for 1.5h;

With benzyl alcohol; In toluene; at 90 ℃; for 3.5h;
DOI:10.1016/j.bmc.2013.06.057

Reference yield: 28.0%

: 100-51-6,185532-71-2
benzyl alcohol

: 534572-20-8
(3S,5R)-1-(tert-butoxycarbonyl)-3-(methoxycarbonyl)piperidine-5-carboxylic acid

: 1448902-04-2
1-tert-butyl 3-methyl (3S,5R)-5-(benzyloxycarbonylamino)piperidine-1,3-dicarboxylate

Guidance literature:: (3S,5R)-1-(tert-butoxycarbonyl)-3-(methoxycarbonyl)piperidine-5-carboxylic acid; With diphenyl phosphoryl azide; triethylamine; In toluene; at 100 ℃; for 1h; Inert atmosphere;

benzyl alcohol; With triethylamine; In toluene; at 80 ℃; for 2h; Inert atmosphere;
DOI:10.1021/acsmedchemlett.9b00445

Reference yield:

: 4591-55-3
dimethyl pyridine-3,5-dicarboxylate

: 1448902-04-2
1-tert-butyl 3-methyl (3S,5R)-5-(benzyloxycarbonylamino)piperidine-1,3-dicarboxylate

Guidance literature:: Multi-step reaction with 4 steps

1.1: hydrogen; hydrogenchloride; 5% rhodium on activated aluminium oxide / methanol; water / 48 h / 50 °C / 150015 Torr

1.2: 16 h / 0 - 20 °C / Inert atmosphere

1.3: 18 h / 20 °C / Inert atmosphere

2.1: acetic anhydride / 2 h / Inert atmosphere; Reflux

3.1: 6'-methoxycinchonan-9-ol / tetrahydrofuran / 6 h / -40 °C

3.2: 19 h / 20 - 80 °C

4.1: triethylamine; diphenyl phosphoryl azide / toluene / 1 h / 100 °C / Inert atmosphere

4.2: 2 h / 80 °C

With hydrogenchloride; diphenyl phosphoryl azide; 5% rhodium on activated aluminium oxide; hydrogen; acetic anhydride; triethylamine; 6'-methoxycinchonan-9-ol; In tetrahydrofuran; methanol; water; toluene;