Benzyl cis-2,3,5,6,7,8-hexahydro-1-hydroxy-6-methyl-2-<(p-tolylsulfonyl)oxy>-8-oxo-1H-pyrrolo<1,2-a>indole-9-carboxylate

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Chemical Name:Benzyl cis-2,3,5,6,7,8-hexahydro-1-hydroxy-6-methyl-2-<(p-tolylsulfonyl)oxy>-8-oxo-1H-pyrrolo<1,2-a>indole-9-carboxylate
CAS No.:93454-41-2
Molecular Formula:C₂₇H₂₇NO₇S
Molecular Weight:509.58
Hs Code.:

Synonyms:

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Chemical Property of Benzyl cis-2,3,5,6,7,8-hexahydro-1-hydroxy-6-methyl-2-<(p-tolylsulfonyl)oxy>-8-oxo-1H-pyrrolo<1,2-a>indole-9-carboxylate

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Technology Process of Benzyl cis-2,3,5,6,7,8-hexahydro-1-hydroxy-6-methyl-2-<(p-tolylsulfonyl)oxy>-8-oxo-1H-pyrrolo<1,2-a>indole-9-carboxylate

There total 11 articles about Benzyl cis-2,3,5,6,7,8-hexahydro-1-hydroxy-6-methyl-2-<(p-tolylsulfonyl)oxy>-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: 32.0%

: 93454-36-5,93528-54-2
Benzyl cis-1,2-Dihydroxy-2,3,5,6,7,8-hexahydro-6-methyl-8-oxo-1H-pyrrolo<1,2-a>indole-9-carboxylate

: 98-59-9
p-toluenesulfonyl chloride

: 93454-41-2,93528-60-0
Benzyl cis-2,3,5,6,7,8-hexahydro-1-hydroxy-6-methyl-2-<(p-tolylsulfonyl)oxy>-8-oxo-1H-pyrrolo<1,2-a>indole-9-carboxylate

Guidance literature:: With pyridine; for 16h; Ambient temperature;
DOI:10.1021/jo00200a031

Reference yield:

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

: 93454-41-2,93528-60-0
Benzyl cis-2,3,5,6,7,8-hexahydro-1-hydroxy-6-methyl-2-<(p-tolylsulfonyl)oxy>-8-oxo-1H-pyrrolo<1,2-a>indole-9-carboxylate

Guidance literature:: Multi-step reaction with 11 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: 53 percent / trifluoroacetic anhydride / tetrahydrofuran / 1 h / 60 °C

10: 1) N-methylmorphine N-oxide, 2.5percent OsO₄ 2) sodium bisulfite / 1) t-BuOH, THF, H₂O, room temperature, 48 h 2) H₂O, room temperature, 20 min

11: 32 percent / pyridine / 16 h / Ambient temperature

With pyridine; hydrogenchloride; sodium hydroxide; osmium(VIII) oxide; sulfuric acid; potassium tert-butylate; sodium methylate; sodium hydrogensulfite; 4-methylmorpholine N-oxide; triethylamine; trifluoroacetic anhydride; In tetrahydrofuran; methanol; water; acetonitrile;
DOI:10.1021/jo00200a031

Reference yield:

: 93454-30-9,93454-31-0,188907-30-4
5,6,7,8-Tetrahydro-6-methyl-8-oxo-3H-pyrrolo<1,2-a>indole-9-carboxylic acid

: 93454-41-2,93528-60-0
Benzyl cis-2,3,5,6,7,8-hexahydro-1-hydroxy-6-methyl-2-<(p-tolylsulfonyl)oxy>-8-oxo-1H-pyrrolo<1,2-a>indole-9-carboxylate

Guidance literature:: Multi-step reaction with 3 steps

1: 53 percent / trifluoroacetic anhydride / tetrahydrofuran / 1 h / 60 °C

2: 1) N-methylmorphine N-oxide, 2.5percent OsO₄ 2) sodium bisulfite / 1) t-BuOH, THF, H₂O, room temperature, 48 h 2) H₂O, room temperature, 20 min

3: 32 percent / pyridine / 16 h / Ambient temperature

With pyridine; osmium(VIII) oxide; sodium hydrogensulfite; 4-methylmorpholine N-oxide; trifluoroacetic anhydride; In tetrahydrofuran;
DOI:10.1021/jo00200a031