(2S,8aS)-4-hydroxy-1-(4-methoxybenzyl)-2-propyl-1,2,6,7,8,8a-hexahydroquinoline-3-carboxylic acid allyl ester

Base Information

Chemical Name:(2S,8aS)-4-hydroxy-1-(4-methoxybenzyl)-2-propyl-1,2,6,7,8,8a-hexahydroquinoline-3-carboxylic acid allyl ester
CAS No.:1342302-14-0
Molecular Formula:C₂₄H₃₁NO₄
Molecular Weight:397.514
Hs Code.:

Synonyms:(2S,8aS)-4-hydroxy-1-(4-methoxybenzyl)-2-propyl-1,2,6,7,8,8a-hexahydroquinoline-3-carboxylic acid allyl ester

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Chemical Property of (2S,8aS)-4-hydroxy-1-(4-methoxybenzyl)-2-propyl-1,2,6,7,8,8a-hexahydroquinoline-3-carboxylic acid allyl ester

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Technology Process of (2S,8aS)-4-hydroxy-1-(4-methoxybenzyl)-2-propyl-1,2,6,7,8,8a-hexahydroquinoline-3-carboxylic acid allyl ester

There total 9 articles about (2S,8aS)-4-hydroxy-1-(4-methoxybenzyl)-2-propyl-1,2,6,7,8,8a-hexahydroquinoline-3-carboxylic acid allyl ester 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:

: C₂HF₃O₂*C₂₀H₂₅NO₄

: 123-72-8
butyraldehyde

: (2R,8aS)-4-hydroxy-1-(4-methoxybenzyl)-2-propyl-1,2,6,7,8,8a-hexahydroquinoline-3-carboxylic acid allyl ester

: 1342302-14-0
(2S,8aS)-4-hydroxy-1-(4-methoxybenzyl)-2-propyl-1,2,6,7,8,8a-hexahydroquinoline-3-carboxylic acid allyl ester

Guidance literature:: With sodium hydrogencarbonate; In methanol; dichloromethane; at 20 ℃; for 48h; optical yield given as %de; diastereoselective reaction; Molecular sieve;
DOI:10.1055/s-0030-1260102

Reference yield:

: 1342302-22-0
C₂₀H₂₉NO₄

: (2R,8aS)-4-hydroxy-1-(4-methoxybenzyl)-2-propyl-1,2,6,7,8,8a-hexahydroquinoline-3-carboxylic acid allyl ester

: 1342302-14-0
(2S,8aS)-4-hydroxy-1-(4-methoxybenzyl)-2-propyl-1,2,6,7,8,8a-hexahydroquinoline-3-carboxylic acid allyl ester

Guidance literature:: Multi-step reaction with 5 steps

1.1: Dess-Martin periodane; triethylamine / dichloromethane / 4 h / 20 °C

2.1: lithium diisopropyl amide / tetrahydrofuran; hexane / 0.5 h / -78 °C

2.2: 12 h / -78 °C

3.1: Dess-Martin periodane / dichloromethane / 12 h / 20 °C

4.1: triethylsilane / dichloromethane / 0.5 h / 20 °C

5.1: sodium hydrogencarbonate / methanol; dichloromethane / 48 h / 20 °C / Molecular sieve

With triethylsilane; sodium hydrogencarbonate; Dess-Martin periodane; triethylamine; lithium diisopropyl amide; In tetrahydrofuran; methanol; hexane; dichloromethane; 1.1: Dess-Martin oxidation / 3.1: Dess-Martin oxidation / 5.1: intramolecular Mannich reaction;
DOI:10.1055/s-0030-1260102

Reference yield:

: 1342302-05-9
(1S)-(2-formylcyclohex-2-enyl)(4-methoxybenzyl)carbamic acid tert-butyl ester

: (2R,8aS)-4-hydroxy-1-(4-methoxybenzyl)-2-propyl-1,2,6,7,8,8a-hexahydroquinoline-3-carboxylic acid allyl ester

: 1342302-14-0
(2S,8aS)-4-hydroxy-1-(4-methoxybenzyl)-2-propyl-1,2,6,7,8,8a-hexahydroquinoline-3-carboxylic acid allyl ester

Guidance literature:: Multi-step reaction with 4 steps

1.1: lithium diisopropyl amide / tetrahydrofuran; hexane / 0.5 h / -78 °C

1.2: 12 h / -78 °C

2.1: Dess-Martin periodane / dichloromethane / 12 h / 20 °C

3.1: triethylsilane / dichloromethane / 0.5 h / 20 °C

4.1: sodium hydrogencarbonate / methanol; dichloromethane / 48 h / 20 °C / Molecular sieve

With triethylsilane; sodium hydrogencarbonate; Dess-Martin periodane; lithium diisopropyl amide; In tetrahydrofuran; methanol; hexane; dichloromethane; 2.1: Dess-Martin oxidation / 4.1: intramolecular Mannich reaction;
DOI:10.1055/s-0030-1260102