Benzyl 2,3,5,6,7,8-Hexahydro-2-<(methylsulfonyl)oxy>-1-methoxy-6-methyl-8-oxo-1H-pyrrolo<1,2-a>indole-9-carboxylate

Base Information

Chemical Name:Benzyl 2,3,5,6,7,8-Hexahydro-2-<(methylsulfonyl)oxy>-1-methoxy-6-methyl-8-oxo-1H-pyrrolo<1,2-a>indole-9-carboxylate
CAS No.:79562-60-0
Molecular Formula:C₂₂H₂₅NO₇S
Molecular Weight:447.509
Hs Code.:

Synonyms:Benzyl 2,3,5,6,7,8-Hexahydro-2-<(methylsulfonyl)oxy>-1-methoxy-6-methyl-8-oxo-1H-pyrrolo<1,2-a>indole-9-carboxylate

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Chemical Property of Benzyl 2,3,5,6,7,8-Hexahydro-2-<(methylsulfonyl)oxy>-1-methoxy-6-methyl-8-oxo-1H-pyrrolo<1,2-a>indole-9-carboxylate

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Technology Process of Benzyl 2,3,5,6,7,8-Hexahydro-2-<(methylsulfonyl)oxy>-1-methoxy-6-methyl-8-oxo-1H-pyrrolo<1,2-a>indole-9-carboxylate

There total 26 articles about Benzyl 2,3,5,6,7,8-Hexahydro-2-<(methylsulfonyl)oxy>-1-methoxy-6-methyl-8-oxo-1H-pyrrolo<1,2-a>indole-9-carboxylate 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: 85.2%

: 100-39-0
benzyl bromide

: 79562-59-7
2,3,5,6,7,8-Hexahydro-2-<(methylsulfonyl)oxy>-1-methoxy-6-methyl-8-oxo-1H-pyrrolo<1,2-a>indole-9-carboxylic acid

: 79562-60-0
Benzyl 2,3,5,6,7,8-Hexahydro-2-<(methylsulfonyl)oxy>-1-methoxy-6-methyl-8-oxo-1H-pyrrolo<1,2-a>indole-9-carboxylate

Guidance literature:: With 18-crown-6 ether; potassium carbonate; In acetone; for 18h; Heating;
DOI:10.1021/jo00200a031

Reference yield:

: 27151-65-1
3-methyl-1,5-pentanedioic acid monomethyl ester

: 79562-60-0
Benzyl 2,3,5,6,7,8-Hexahydro-2-<(methylsulfonyl)oxy>-1-methoxy-6-methyl-8-oxo-1H-pyrrolo<1,2-a>indole-9-carboxylate

Guidance literature:: Multi-step reaction with 12 steps

2: 1)a) Ac₂O, 60 deg C, 15 min b) 80 deg C, 30 min 2) 135 deg C, 3 h

3: 94 percent / 2percent sodium methoxide / methanol / 1 h / Ambient temperature

4: 1) potassium tert-butoxide 2) 10percent HCl / 1) THF, room temperature, 30 min 2) water, 0 deg C

5: NaOH / methanol; H₂O / Ambient temperature

6: 6 N H₂SO₄ / methanol; H₂O / 1 h / 0 °C

7: 82.7 percent / Et₃N / tetrahydrofuran; acetonitrile / 1) 0 deg C, 1 min 2) room temperature, 30 min

8: 1) 2percent NaOMe 2) 10percent HCl / 1) methanol, reflux, 4 h 2) 0 deg C

9: 74.3 percent / Br₂ / tetrahydrofuran; H₂O / 1.5 h / Ambient temperature

10: 2) 10percent HCl / 1) room temperature, 1 h

11: 74 percent / Et₃N / tetrahydrofuran / 1) 0 deg C 2) room temperature

12: 85.2 percent / K₂CO₃, 18-crown-6 / acetone / 18 h / Heating

With hydrogenchloride; sodium hydroxide; 18-crown-6 ether; sulfuric acid; potassium tert-butylate; bromine; sodium methylate; potassium carbonate; triethylamine; In tetrahydrofuran; methanol; water; acetone; acetonitrile;
DOI:10.1021/jo00200a031

Reference yield:

: 27151-65-1
3-methyl-1,5-pentanedioic acid monomethyl ester

: 79562-60-0,93528-71-3,93528-72-4,93528-73-5,93528-74-6
Benzyl cis-2,3,5,6,7,8-Hexahydro-2-<(methylsulfonyl)oxy>-1-methoxy-6-methyl-8-oxo-1H-pyrrolo<1,2-a>indole-9-carboxylate

Guidance literature:: Multi-step reaction with 12 steps

2: 1)a) Ac₂O, 60 deg C, 15 min b) 80 deg C, 30 min 2) 135 deg C, 3 h

3: 94 percent / 2percent sodium methoxide / methanol / 1 h / Ambient temperature

4: 1) potassium tert-butoxide 2) 10percent HCl / 1) THF, room temperature, 30 min 2) water, 0 deg C

5: NaOH / methanol; H₂O / Ambient temperature

6: 6 N H₂SO₄ / methanol; H₂O / 1 h / 0 °C

7: 82.7 percent / Et₃N / tetrahydrofuran; acetonitrile / 1) 0 deg C, 1 min 2) room temperature, 30 min

8: 1) 2percent NaOMe 2) 10percent HCl / 1) methanol, reflux, 4 h 2) 0 deg C

9: 74.3 percent / Br₂ / tetrahydrofuran; H₂O / 1.5 h / Ambient temperature

10: 2) 10percent HCl / 1) room temperature, 1 h

11: 74 percent / Et₃N / tetrahydrofuran / 1) 0 deg C 2) room temperature

12: K₂CO₃, 18-crown-6 / acetone / 18 h / Heating

With hydrogenchloride; sodium hydroxide; 18-crown-6 ether; sulfuric acid; potassium tert-butylate; bromine; sodium methylate; potassium carbonate; triethylamine; In tetrahydrofuran; methanol; water; acetone; acetonitrile;
DOI:10.1021/jo00200a031