1-(S)-(N-carbobenzyloxy)amino-1,2,3,4,6,7,12,12b-(R)-octahydroindolo<2,3-a>quinolizidin-4-one

Base Information

Chemical Name:1-(S)-(N-carbobenzyloxy)amino-1,2,3,4,6,7,12,12b-(R)-octahydroindolo<2,3-a>quinolizidin-4-one
CAS No.:153037-23-1
Molecular Formula:C₂₃H₂₃N₃O₃
Molecular Weight:389.454
Hs Code.:

Synonyms:1-(S)-(N-carbobenzyloxy)amino-1,2,3,4,6,7,12,12b-(R)-octahydroindolo<2,3-a>quinolizidin-4-one

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Chemical Property of 1-(S)-(N-carbobenzyloxy)amino-1,2,3,4,6,7,12,12b-(R)-octahydroindolo<2,3-a>quinolizidin-4-one

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Technology Process of 1-(S)-(N-carbobenzyloxy)amino-1,2,3,4,6,7,12,12b-(R)-octahydroindolo<2,3-a>quinolizidin-4-one

There total 6 articles about 1-(S)-(N-carbobenzyloxy)amino-1,2,3,4,6,7,12,12b-(R)-octahydroindolo<2,3-a>quinolizidin-4-one 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: 81.0%

: 153037-22-0
1(R)-4'(S)-benzyloxycarbonylamino-4'-(1,2,3,4-tetrahydro-1H-β-carbolin-1-yl)butyric acid tert-butyl ester

: 153037-23-1
1-(S)-(N-carbobenzyloxy)amino-1,2,3,4,6,7,12,12b-(R)-octahydroindolo<2,3-a>quinolizidin-4-one

Guidance literature:: With sodium methylate; In methanol; for 24h; Ambient temperature;
DOI:10.1016/S0040-4020(01)96265-9

Reference yield:

: 3886-08-6
5-tert-butyl N-benzyloxycarbonyl-L-glutamate

: 153037-23-1
1-(S)-(N-carbobenzyloxy)amino-1,2,3,4,6,7,12,12b-(R)-octahydroindolo<2,3-a>quinolizidin-4-one

Guidance literature:: Multi-step reaction with 4 steps

1.1: N-methylmorpholine; iso-butyl chloroformate / CH₂Cl₂ / 0.5 h / -15 °C

1.2: 96 percent / CH₂Cl₂ / 2 h / -15 - 20 °C

2.1: 99 percent / LiAlH₄ / diethyl ether / 2.67 h / -40 °C

3.1: 81 percent / TFA / CH₂Cl₂ / 2 h / -40 °C

4.1: NaOMe / methanol / 24 h / 20 °C

With 4-methyl-morpholine; lithium aluminium tetrahydride; sodium methylate; trifluoroacetic acid; isobutyl chloroformate; In methanol; diethyl ether; dichloromethane; 1.1: Substitution / 1.2: Substitution / 2.1: Reduction / 3.1: Pictet-Spengler reaction / 4.1: Cyclization;
DOI:10.1016/S0040-4020(00)00165-4

Reference yield:

: 92506-78-0
4(S)-benzyloxycarbonylamino-5-oxo-pentanoic acid tert-butyl ester

: 153037-23-1
1-(S)-(N-carbobenzyloxy)amino-1,2,3,4,6,7,12,12b-(R)-octahydroindolo<2,3-a>quinolizidin-4-one

Guidance literature:: Multi-step reaction with 2 steps

1: 81 percent / TFA / CH₂Cl₂ / 2 h / -40 °C

2: NaOMe / methanol / 24 h / 20 °C

With sodium methylate; trifluoroacetic acid; In methanol; dichloromethane; 1: Pictet-Spengler reaction / 2: Cyclization;
DOI:10.1016/S0040-4020(00)00165-4