Benzoic acid (3aR,9R,9aS,9bS)-2,2-dimethyl-octahydro-[1,3]dioxolo[4,5-a]indolizin-9-yl ester

Base Information

Chemical Name:Benzoic acid (3aR,9R,9aS,9bS)-2,2-dimethyl-octahydro-[1,3]dioxolo[4,5-a]indolizin-9-yl ester
CAS No.:105888-90-2
Molecular Formula:C₁₈H₂₃NO₄
Molecular Weight:317.385
Hs Code.:

Synonyms:Benzoic acid (3aR,9R,9aS,9bS)-2,2-dimethyl-octahydro-[1,3]dioxolo[4,5-a]indolizin-9-yl ester

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Chemical Property of Benzoic acid (3aR,9R,9aS,9bS)-2,2-dimethyl-octahydro-[1,3]dioxolo[4,5-a]indolizin-9-yl ester

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Technology Process of Benzoic acid (3aR,9R,9aS,9bS)-2,2-dimethyl-octahydro-[1,3]dioxolo[4,5-a]indolizin-9-yl ester

There total 39 articles about Benzoic acid (3aR,9R,9aS,9bS)-2,2-dimethyl-octahydro-[1,3]dioxolo[4,5-a]indolizin-9-yl 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:

: 17460-38-7
methyl 3-azido-4,6-O-benzylidene-3-deoxy-α-D-altropyranoside

: 105888-90-2,107794-67-2
Benzoic acid (3aR,9S,9aS,9bS)-2,2-dimethyl-octahydro-[1,3]dioxolo[4,5-a]indolizin-9-yl ester

Guidance literature:: Multi-step reaction with 15 steps

1: 1.) NaH / 1.) DMF, 0 deg C, 5 min, 2.) RT, 1 h

2: 80percent aq. acetic acid / 4 h / 100 °C

3: concd. H₂SO₄ / 4 h / Ambient temperature

4: 82 percent / sodium methoxide / methanol / 0.08 h / Ambient temperature

5: 64 percent / pyridine, triethylamine / 6 h / Ambient temperature

6: 60 percent / benzene / 3 h / Heating

7: 88 percent / camphorsulfonic acid / acetone / 2 h / Ambient temperature

8: H₂ / Raney nickel W-4 / ethanol / 36 h / 760 Torr / Ambient temperature

9: Bu₄NF / tetrahydrofuran / 4 h / Ambient temperature

10: pyridine / 3 h / 40 °C

11: K₂CO₃ / dioxane; H₂O / 2 h / 90 °C

12: 64 percent / cyclohexene, 20percent Pd(OH)2/C / ethanol / 26 h / Heating

13: 83 percent / pyridine / 4 h / Ambient temperature

14: 84 percent / dimethylformamide / 0.5 h / 140 °C

15: BH₃-Me₂S / tetrahydrofuran / 2 h / Ambient temperature

With pyridine; palladium dihydroxide; dimethylsulfide borane complex; sulfuric acid; camphor-10-sulfonic acid; tetrabutyl ammonium fluoride; hydrogen; sodium methylate; sodium hydride; potassium carbonate; acetic acid; triethylamine; cyclohexene; Raney nickel W-4; In tetrahydrofuran; 1,4-dioxane; methanol; ethanol; water; N,N-dimethyl-formamide; acetone; benzene;
DOI:10.1021/jo00257a003

Reference yield:

: 39032-45-6
methyl 3-azido-2-O-benzyl-4,6-O-benzylidene-3-deoxy-α-D-altropyranoside

: 105888-90-2,107794-67-2
Benzoic acid (3aR,9S,9aS,9bS)-2,2-dimethyl-octahydro-[1,3]dioxolo[4,5-a]indolizin-9-yl ester

Guidance literature:: Multi-step reaction with 14 steps

1: 80percent aq. acetic acid / 4 h / 100 °C

2: concd. H₂SO₄ / 4 h / Ambient temperature

3: 82 percent / sodium methoxide / methanol / 0.08 h / Ambient temperature

4: 64 percent / pyridine, triethylamine / 6 h / Ambient temperature

5: 60 percent / benzene / 3 h / Heating

6: 88 percent / camphorsulfonic acid / acetone / 2 h / Ambient temperature

7: H₂ / Raney nickel W-4 / ethanol / 36 h / 760 Torr / Ambient temperature

8: Bu₄NF / tetrahydrofuran / 4 h / Ambient temperature

9: pyridine / 3 h / 40 °C

10: K₂CO₃ / dioxane; H₂O / 2 h / 90 °C

11: 64 percent / cyclohexene, 20percent Pd(OH)2/C / ethanol / 26 h / Heating

12: 83 percent / pyridine / 4 h / Ambient temperature

13: 84 percent / dimethylformamide / 0.5 h / 140 °C

14: BH₃-Me₂S / tetrahydrofuran / 2 h / Ambient temperature

With pyridine; palladium dihydroxide; dimethylsulfide borane complex; sulfuric acid; camphor-10-sulfonic acid; tetrabutyl ammonium fluoride; hydrogen; sodium methylate; potassium carbonate; acetic acid; triethylamine; cyclohexene; Raney nickel W-4; In tetrahydrofuran; 1,4-dioxane; methanol; ethanol; water; N,N-dimethyl-formamide; acetone; benzene;
DOI:10.1021/jo00257a003

Reference yield:

: (2R,3S,4R,5S,6S)-4-Azido-5-benzyloxy-2-hydroxymethyl-6-methoxy-tetrahydro-pyran-3-ol

: 105888-90-2,107794-67-2
Benzoic acid (3aR,9S,9aS,9bS)-2,2-dimethyl-octahydro-[1,3]dioxolo[4,5-a]indolizin-9-yl ester

Guidance literature:: Multi-step reaction with 13 steps

1: concd. H₂SO₄ / 4 h / Ambient temperature

2: 82 percent / sodium methoxide / methanol / 0.08 h / Ambient temperature

3: 64 percent / pyridine, triethylamine / 6 h / Ambient temperature

4: 60 percent / benzene / 3 h / Heating

5: 88 percent / camphorsulfonic acid / acetone / 2 h / Ambient temperature

6: H₂ / Raney nickel W-4 / ethanol / 36 h / 760 Torr / Ambient temperature

7: Bu₄NF / tetrahydrofuran / 4 h / Ambient temperature

8: pyridine / 3 h / 40 °C

9: K₂CO₃ / dioxane; H₂O / 2 h / 90 °C

10: 64 percent / cyclohexene, 20percent Pd(OH)2/C / ethanol / 26 h / Heating

11: 83 percent / pyridine / 4 h / Ambient temperature

12: 84 percent / dimethylformamide / 0.5 h / 140 °C

13: BH₃-Me₂S / tetrahydrofuran / 2 h / Ambient temperature

With pyridine; palladium dihydroxide; dimethylsulfide borane complex; sulfuric acid; camphor-10-sulfonic acid; tetrabutyl ammonium fluoride; hydrogen; sodium methylate; potassium carbonate; triethylamine; cyclohexene; Raney nickel W-4; In tetrahydrofuran; 1,4-dioxane; methanol; ethanol; water; N,N-dimethyl-formamide; acetone; benzene;
DOI:10.1021/jo00257a003