3-benzyloxymethyl-2,3,7,7a,8,9,10,11-octahydro-1H-pyrrolo[2,1-j]quinoline

Base Information

• Chemical Name: 3-benzyloxymethyl-2,3,7,7a,8,9,10,11-octahydro-1H-pyrrolo[2,1-j]quinoline
• CAS No.: 879572-79-9
• Molecular Formula: C₂₀H₂₇NO
• Molecular Weight: 297.44
• Mol file: 879572-79-9.mol

Synonyms:3-benzyloxymethyl-2,3,7,7a,8,9,10,11-octahydro-1H-pyrrolo[2,1-j]quinoline

Chemical Property of 3-benzyloxymethyl-2,3,7,7a,8,9,10,11-octahydro-1H-pyrrolo[2,1-j]quinoline

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 3-benzyloxymethyl-2,3,7,7a,8,9,10,11-octahydro-1H-pyrrolo[2,1-j]quinoline

There total 16 articles about 3-benzyloxymethyl-2,3,7,7a,8,9,10,11-octahydro-1H-pyrrolo[2,1-j]quinoline 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:

(2S,5R,10S)-tert-butyl 5-(benzyloxymethyl)-10-[3'-(tert-butyldiphenylsilanyloxy)propyl]-1-azaspiro[4,5]dec-6-ene-1-carboxylate (879572-75-5) → 3-benzyloxymethyl-2,3,7,7a,8,9,10,11-octahydro-1H-pyrrolo[2,1-j]quinoline (879572-79-9)

Guidance literature:

Multi-step reaction with 4 steps

1: 95 percent / hydrogen; triethylamine / Pd/C / methanol / 12 h / 20 °C

2: 99 percent / tetrabutylammonium fluoride / tetrahydrofuran / 12 h / 20 °C

3: 96 percent / NaHCO₃; Dess-Martin periodinane / CH₂Cl₂ / 0.5 h / 0 °C

4: p-TsOH*H₂O / acetone; H₂O / 5 h / Heating

With tetrabutyl ammonium fluoride; hydrogen; sodium hydrogencarbonate; Dess-Martin periodane; toluene-4-sulfonic acid; triethylamine; palladium on activated charcoal; In tetrahydrofuran; methanol; dichloromethane; water; acetone;

DOI:10.1021/ol053010j

Reference yield:

(2S,5S)-tert-butyl 5-(benzyloxymethyl)-2-[(S)-1-(tert-butyldiphenylsilyloxy)oct-7-en-4-yl]-2-vinylpyrrolidine-1-carboxylate (879572-72-2) → 3-benzyloxymethyl-2,3,7,7a,8,9,10,11-octahydro-1H-pyrrolo[2,1-j]quinoline (879572-79-9)

Guidance literature:

Multi-step reaction with 5 steps

1: 98 percent / second generation Grubbs' catalyst / CH₂Cl₂ / 1 h / 40 °C

2: 95 percent / hydrogen; triethylamine / Pd/C / methanol / 12 h / 20 °C

3: 99 percent / tetrabutylammonium fluoride / tetrahydrofuran / 12 h / 20 °C

4: 96 percent / NaHCO₃; Dess-Martin periodinane / CH₂Cl₂ / 0.5 h / 0 °C

5: p-TsOH*H₂O / acetone; H₂O / 5 h / Heating

With tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride; tetrabutyl ammonium fluoride; hydrogen; sodium hydrogencarbonate; Dess-Martin periodane; toluene-4-sulfonic acid; triethylamine; palladium on activated charcoal; In tetrahydrofuran; methanol; dichloromethane; water; acetone;

DOI:10.1021/ol053010j

Reference yield:

(2-aminophenyl)-(6-vinyl-1-azaspiro[4.5]dec-1-yl)methanone → 3-benzyloxymethyl-2,3,7,7a,8,9,10,11-octahydro-1H-pyrrolo[2,1-j]quinoline (879572-79-9)

Guidance literature:

Multi-step reaction with 8 steps

1.1: 81 percent / NaNO₂; HCl; CuCl / 4 Angstroem molecular sieves / methanol / 1.5 h / 18 °C

2.1: 76 percent / BF₃*Et₂O; CuBr₂*Me₂S / diethyl ether / 4 h / -78 - 20 °C

3.1: BF₃*2AcOH / CH₂Cl₂ / 0.25 h / 20 °C

3.2: 95 percent / NaHCO₃; aq. H₂O₂ / methanol; tetrahydrofuran / Heating

4.1: H₂; Rh(CO)2acac; P(OPh)3 / tetrahydrofuran / 6 h / 60 °C / 3040.2 Torr

5.1: 77 mg / HCl / methanol / 0.17 h / 20 °C

6.1: 99 percent / LiOH*H₂O / ethanol / 168 h / Heating

7.1: 75 percent / NaH / tetrahydrofuran / 72 h / 20 °C

8.1: p-TsOH*H₂O / acetone; H₂O / 3 h / Heating

With triphenyl phosphite; hydrogenchloride; acetylacetonatodicarbonylrhodium(l); lithium hydroxide; copper bromide dimethyl sulfide complex; boron trifluoride diethyl etherate; hydrogen; boron trifluoride diacetate; sodium hydride; toluene-4-sulfonic acid; copper(l) chloride; sodium nitrite; 4 A molecular sieve; In tetrahydrofuran; methanol; diethyl ether; ethanol; dichloromethane; water; acetone; 3.2: Tamao oxidation;

DOI:10.1021/jo0201070

upstream raw materials:

2-benzyloxymethyl-6-(3,3-dimethoxypropyl)-1-azaspiro[4.5]decane

(2S,5S,6S)-tert-butyl 2-(benzyloxymethyl)-6-(3'-oxo-propyl)-1-azaspiro[4,5]decane-1-carboxylate

(2S,5S,6S)-tert-butyl 2-(benzyloxymethyl)-6-(3'-hydroxypropyl)-1-azaspiro[4,5]decane-1-carboxylate

(2S,5R,10S)-tert-butyl 5-(benzyloxymethyl)-10-[3'-(tert-butyldiphenylsilanyloxy)propyl]-1-azaspiro[4,5]dec-6-ene-1-carboxylate

Downstream raw materials:

(2S,5S,7aS,11aS)-3-(benzyloxymethyl)decahydro-1H-pyrrolo[1,2-j]quinoline-5-carbonitrile

(3S,5S,7aS,11′S)-3-(benzyloxymethyl)-5-hexyldecahydro-1H-pyrrolo[1,2-j]quinoline

(3S,5R,7aS,11aS)-3-benzyloxymethyl-5-hexyldecahydro-H-pyrrolo[2,1-j]quinoline