(3S,5R,7S,7aR,11aR)-3-[(benzyloxy)methyl]-5-hexyldecahydro-1H-pyrrolo[2,1-j]quinolin-7-ol

Base Information

Chemical Name:(3S,5R,7S,7aR,11aR)-3-[(benzyloxy)methyl]-5-hexyldecahydro-1H-pyrrolo[2,1-j]quinolin-7-ol
CAS No.:844698-95-9
Molecular Formula:C₂₆H₄₁NO₂
Molecular Weight:399.617
Hs Code.:

Synonyms:(3S,5R,7S,7aR,11aR)-3-[(benzyloxy)methyl]-5-hexyldecahydro-1H-pyrrolo[2,1-j]quinolin-7-ol

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Chemical Property of (3S,5R,7S,7aR,11aR)-3-[(benzyloxy)methyl]-5-hexyldecahydro-1H-pyrrolo[2,1-j]quinolin-7-ol

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Technology Process of (3S,5R,7S,7aR,11aR)-3-[(benzyloxy)methyl]-5-hexyldecahydro-1H-pyrrolo[2,1-j]quinolin-7-ol

There total 9 articles about (3S,5R,7S,7aR,11aR)-3-[(benzyloxy)methyl]-5-hexyldecahydro-1H-pyrrolo[2,1-j]quinolin-7-ol 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: 84.0%

: 844698-94-8
tert-butyl (2S,5S,6R)-2-[(benzyloxy)methyl]-6-{(1S,3S)-1-hydroxy-3-[(methylsulfonyl)oxy]nonyl}-1-azaspiro[4.5]decane-1-carboxylate

: 844698-95-9
(3S,5R,7S,7aR,11aR)-3-[(benzyloxy)methyl]-5-hexyldecahydro-1H-pyrrolo[2,1-j]quinolin-7-ol

Guidance literature:: With trifluoroacetic acid; In dichloromethane; at 20 ℃; for 0.5h;
DOI:10.1021/ja040213e

Reference yield:

: 484061-51-0
tert-butyl (2S,5S,6S)-2-benzyloxymethyl-6-[(1E)-3-oxonon-1-enyl]-1-azaspiro[4.5]decane-1-carboxylate

: 844698-95-9
(3S,5R,7S,7aR,11aR)-3-[(benzyloxy)methyl]-5-hexyldecahydro-1H-pyrrolo[2,1-j]quinolin-7-ol

Guidance literature:: Multi-step reaction with 5 steps

1: 92 percent / LiAlH₄; (S)-1,1'-binaphthol; ethanol / tetrahydrofuran / 5 h / -78 °C

2: 68 percent / m-chloroperbenzoic acid; sodium hydrogen phosphate / CH₂Cl₂ / 4 h / 0 °C

3: 84 percent / LiAlH₄ / diethyl ether / 4 h / 20 °C

4: 73 percent / Et₃N; 4-dimethylaminopyridine / CH₂Cl₂ / 1 h / 20 °C

5: 84 percent / TFA / CH₂Cl₂ / 0.5 h / 20 °C

With dmap; disodium hydrogenphosphate; lithium aluminium tetrahydride; ethanol; (S)-[1,1']-binaphthalenyl-2,2'-diol; triethylamine; 3-chloro-benzenecarboperoxoic acid; trifluoroacetic acid; In tetrahydrofuran; diethyl ether; dichloromethane;
DOI:10.1021/ja040213e

Reference yield:

: 484061-49-6
tert-butyl (2S,5S,6S)-2-benzyloxymethyl-6-[(1E,3S/R)-3-hydroxynon-1-enyl]-1-azaspiro[4.5]decane-1-carboxylate

: 844698-95-9
(3S,5R,7S,7aR,11aR)-3-[(benzyloxy)methyl]-5-hexyldecahydro-1H-pyrrolo[2,1-j]quinolin-7-ol

Guidance literature:: Multi-step reaction with 6 steps

1: 91 percent / MnO₂ / CH₂Cl₂ / 3 h / 20 °C

2: 92 percent / LiAlH₄; (S)-1,1'-binaphthol; ethanol / tetrahydrofuran / 5 h / -78 °C

3: 68 percent / m-chloroperbenzoic acid; sodium hydrogen phosphate / CH₂Cl₂ / 4 h / 0 °C

4: 84 percent / LiAlH₄ / diethyl ether / 4 h / 20 °C

5: 73 percent / Et₃N; 4-dimethylaminopyridine / CH₂Cl₂ / 1 h / 20 °C

6: 84 percent / TFA / CH₂Cl₂ / 0.5 h / 20 °C

With dmap; manganese(IV) oxide; disodium hydrogenphosphate; lithium aluminium tetrahydride; ethanol; (S)-[1,1']-binaphthalenyl-2,2'-diol; triethylamine; 3-chloro-benzenecarboperoxoic acid; trifluoroacetic acid; In tetrahydrofuran; diethyl ether; dichloromethane;
DOI:10.1021/ja040213e