(3aR,7aR)-5-benzyl-2,2-dimethyl-7-methylenehexahydro-[1,3]dioxolo[4,5-c]pyridine

Base Information

Chemical Name:(3aR,7aR)-5-benzyl-2,2-dimethyl-7-methylenehexahydro-[1,3]dioxolo[4,5-c]pyridine
CAS No.:319924-33-9
Molecular Formula:C₁₆H₂₁NO₂
Molecular Weight:259.348
Hs Code.:

Synonyms:(3aR,7aR)-5-benzyl-2,2-dimethyl-7-methylenehexahydro-[1,3]dioxolo[4,5-c]pyridine

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Chemical Property of (3aR,7aR)-5-benzyl-2,2-dimethyl-7-methylenehexahydro-[1,3]dioxolo[4,5-c]pyridine

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Technology Process of (3aR,7aR)-5-benzyl-2,2-dimethyl-7-methylenehexahydro-[1,3]dioxolo[4,5-c]pyridine

There total 8 articles about (3aR,7aR)-5-benzyl-2,2-dimethyl-7-methylenehexahydro-[1,3]dioxolo[4,5-c]pyridine 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: 60.0%

: 319924-32-8
1-[Benzyl(trimethylsilylmethyl)amino]-1,4,5-trideoxy-2,3-O-(1-methylethylidene)-D-threo-pent-4-ynitol

: 319924-33-9
(3aR,7aR)-5-benzyl-2,2-dimethyl-7-methylenehexahydro-[1,3]dioxolo[4,5-c]pyridine

Guidance literature:: With naphthalene-1,4-dicarbonitrile; In isopropyl alcohol; for 1.5h; Irradiation;
DOI:10.1016/S0040-4039(00)01553-7

Reference yield:

: 125993-65-9
(4S,5R)-5-(((tert-butyldimethylsilyl)oxy)methyl)-2,2-dimethyl-1,3-dioxolane-4-carbaldehyde

: 319924-33-9
(3aR,7aR)-5-benzyl-2,2-dimethyl-7-methylenehexahydro-[1,3]dioxolo[4,5-c]pyridine

Guidance literature:: Multi-step reaction with 6 steps

1: 65 percent / Ph₃P / CH₂Cl₂ / 2 h / 0 °C

2: 90 percent / BuLi / tetrahydrofuran; hexane / 1 h / -78 °C

3: 85 percent / TBAF / tetrahydrofuran / 4 h / 0 - 20 °C

4: 660 mg / CBr₄; Ph₃P / CH₂Cl₂ / 1 h / 0 - 20 °C

5: 65 percent / K₂CO₃; TBAI / acetonitrile / 96 h / Heating

6: 60 percent / 1,4-dicyanonaphthalene / propan-2-ol / 1.5 h / UV-irradiation

With n-butyllithium; carbon tetrabromide; naphthalene-1,4-dicarbonitrile; tetrabutyl ammonium fluoride; tetra-(n-butyl)ammonium iodide; potassium carbonate; triphenylphosphine; In tetrahydrofuran; hexane; dichloromethane; isopropyl alcohol; acetonitrile;
DOI:10.1055/s-2001-15063

Reference yield:

: 319924-30-6
5-[(tert-Butyldimethylsilyl)oxy]-1,2-dideoxy-3,4-O-(1-methylethylidene)-D-threo-pent-1-yne

: 319924-33-9
(3aR,7aR)-5-benzyl-2,2-dimethyl-7-methylenehexahydro-[1,3]dioxolo[4,5-c]pyridine

Guidance literature:: Multi-step reaction with 4 steps

1: 85 percent / TBAF / tetrahydrofuran / 4 h / 0 - 20 °C

2: 660 mg / CBr₄; Ph₃P / CH₂Cl₂ / 1 h / 0 - 20 °C

3: 65 percent / K₂CO₃; TBAI / acetonitrile / 96 h / Heating

4: 60 percent / 1,4-dicyanonaphthalene / propan-2-ol / 1.5 h / UV-irradiation

With carbon tetrabromide; naphthalene-1,4-dicarbonitrile; tetrabutyl ammonium fluoride; tetra-(n-butyl)ammonium iodide; potassium carbonate; triphenylphosphine; In tetrahydrofuran; dichloromethane; isopropyl alcohol; acetonitrile;
DOI:10.1055/s-2001-15063