(3S,5R,7aS,11aS)-3-[(benzyloxy)methyl]-5-hexyloctahydro-1H-pyrrolo[2,1-j]quinolin-7(7aH)-one

Base Information

Chemical Name:(3S,5R,7aS,11aS)-3-[(benzyloxy)methyl]-5-hexyloctahydro-1H-pyrrolo[2,1-j]quinolin-7(7aH)-one
CAS No.:844698-97-1
Molecular Formula:C₂₆H₃₉NO₂
Molecular Weight:397.601
Hs Code.:

Synonyms:(3S,5R,7aS,11aS)-3-[(benzyloxy)methyl]-5-hexyloctahydro-1H-pyrrolo[2,1-j]quinolin-7(7aH)-one

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Chemical Property of (3S,5R,7aS,11aS)-3-[(benzyloxy)methyl]-5-hexyloctahydro-1H-pyrrolo[2,1-j]quinolin-7(7aH)-one

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Technology Process of (3S,5R,7aS,11aS)-3-[(benzyloxy)methyl]-5-hexyloctahydro-1H-pyrrolo[2,1-j]quinolin-7(7aH)-one

There total 19 articles about (3S,5R,7aS,11aS)-3-[(benzyloxy)methyl]-5-hexyloctahydro-1H-pyrrolo[2,1-j]quinolin-7(7aH)-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: 86.0%

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

: 844698-97-1
(3S,5R,7aS,11aS)-3-[(benzyloxy)methyl]-5-hexyloctahydro-1H-pyrrolo[2,1-j]quinolin-7(7aH)-one

Guidance literature:: (3S,5R,7S,7aR,11aR)-3-[(benzyloxy)methyl]-5-hexyldecahydro-1H-pyrrolo[2,1-j]quinolin-7-ol; With oxalyl dichloride; dimethyl sulfoxide; triethylamine; In dichloromethane; at -78 - 20 ℃;

With potassium carbonate; In methanol; for 2h;
DOI:10.1021/ja040213e

Reference yield: 81.0%

: 748781-37-5
(2S,5S,6R)-2-Benzyloxymethyl-6-((Z)-non-2-enoyl)-1-aza-spiro[4.5]decane-1-carboxylic acid tert-butyl ester

: 844698-97-1
(3S,5R,7aS,11aS)-3-[(benzyloxy)methyl]-5-hexyloctahydro-1H-pyrrolo[2,1-j]quinolin-7(7aH)-one

Guidance literature:: (2S,5S,6R)-2-Benzyloxymethyl-6-((Z)-non-2-enoyl)-1-aza-spiro[4.5]decane-1-carboxylic acid tert-butyl ester; With trifluoroacetic acid; In dichloromethane; at 0 ℃;

With sodium hydrogencarbonate; at 20 ℃; Further stages.;
DOI:10.1016/j.tetlet.2004.05.142

Reference yield:

: 152500-21-5
(S)-5-benzyloxymetyl-1-tert-butoxycarbonyl-2-pyrrolidinone

: 844698-97-1
(3S,5R,7aS,11aS)-3-[(benzyloxy)methyl]-5-hexyloctahydro-1H-pyrrolo[2,1-j]quinolin-7(7aH)-one

Guidance literature:: Multi-step reaction with 8 steps

1.1: 79 percent / tetrahydrofuran / 2 h / 0 °C

2.1: 88 percent / tetrahydrofuran; toluene / 2 h / 0 °C

3.1: aq. K₂CO₃ / methanol / 2 h / 20 °C

4.1: 68 percent / m-chloroperbenzoic acid; sodium hydrogen phosphate / CH₂Cl₂ / 4 h / 0 °C

5.1: 84 percent / LiAlH₄ / diethyl ether / 4 h / 20 °C

6.1: 73 percent / Et₃N; 4-dimethylaminopyridine / CH₂Cl₂ / 1 h / 20 °C

7.1: 84 percent / TFA / CH₂Cl₂ / 0.5 h / 20 °C

8.1: oxalyl chloride; DMSO; Et₃N / CH₂Cl₂ / -78 - 20 °C

8.2: 86 percent / aq. K₂CO₃ / methanol / 2 h

With dmap; disodium hydrogenphosphate; lithium aluminium tetrahydride; oxalyl dichloride; potassium carbonate; dimethyl sulfoxide; triethylamine; 3-chloro-benzenecarboperoxoic acid; trifluoroacetic acid; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; toluene; 8.1: Swern oxidation;
DOI:10.1021/ja040213e