tert-butyl (4aS,7aR)-2-benzamido-7a-phenyl-4,4a,5,7-tetrahydropyrrolo[3,4-d][1,3]thiazine-6-carboxylate

Base Information

Chemical Name:tert-butyl (4aS,7aR)-2-benzamido-7a-phenyl-4,4a,5,7-tetrahydropyrrolo[3,4-d][1,3]thiazine-6-carboxylate
CAS No.:1463486-13-6
Molecular Formula:C₂₄H₂₇N₃O₃S
Molecular Weight:437.563
Hs Code.:

Synonyms:tert-butyl (4aS,7aR)-2-benzamido-7a-phenyl-4,4a,5,7-tetrahydropyrrolo[3,4-d][1,3]thiazine-6-carboxylate

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Chemical Property of tert-butyl (4aS,7aR)-2-benzamido-7a-phenyl-4,4a,5,7-tetrahydropyrrolo[3,4-d][1,3]thiazine-6-carboxylate

Chemical Property:

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Technology Process of tert-butyl (4aS,7aR)-2-benzamido-7a-phenyl-4,4a,5,7-tetrahydropyrrolo[3,4-d][1,3]thiazine-6-carboxylate

There total 10 articles about tert-butyl (4aS,7aR)-2-benzamido-7a-phenyl-4,4a,5,7-tetrahydropyrrolo[3,4-d][1,3]thiazine-6-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: 37.0%

: racemic tert-butyl 2-benzamido-7a-phenyl-4,4a,5,7-tetrahydropyrrolo[3,4-d][1,3]thiazine-6-carboxylate

: tert-butyl (4aR,7aS)-2-benzamido-7a-phenyl-4,4a,5,7-tetrahydropyrrolo[3,4-d][1,3]thiazine-6-carboxylate

: 1463486-13-6
tert-butyl (4aS,7aR)-2-benzamido-7a-phenyl-4,4a,5,7-tetrahydropyrrolo[3,4-d][1,3]thiazine-6-carboxylate

Guidance literature:: With SFC (Supercritical Fluid Chromatography) (Chiralpak AD; Reagent/catalyst; Resolution of racemate;

Reference yield:

: 3182-77-2
N-allylglycine

: tert-butyl (4aR,7aS)-2-benzamido-7a-phenyl-4,4a,5,7-tetrahydropyrrolo[3,4-d][1,3]thiazine-6-carboxylate

: 1463486-13-6
tert-butyl (4aS,7aR)-2-benzamido-7a-phenyl-4,4a,5,7-tetrahydropyrrolo[3,4-d][1,3]thiazine-6-carboxylate

Guidance literature:: Multi-step reaction with 9 steps

1.1: triethylamine / ethanol / 0 - 20 °C

1.2: 3 h / 20 °C

2.1: triethylamine / tetrahydrofuran / 3 h / 0 - 20 °C

2.2: 3 h / 0 - 20 °C

3.1: tetrahydrofuran; diethyl ether / -20 °C

4.1: sodium acetate; hydroxylamine hydrochloride / ethanol / 18 h / 70 °C

5.1: 5,5-dimethyl-1,3-cyclohexadiene / 22 h / 100 - 130 °C

6.1: hydrogen / methanol / 20 °C / 760.05 Torr

7.1: tetrahydrofuran / 0 - 20 °C

8.1: 1-chloro-1-(dimethylamino)-2-methyl-1-propene / dichloromethane / 4 h / 0 - 20 °C / Inert atmosphere

9.1: SFC (Supercritical Fluid Chromatography) (Chiralpak AD / Resolution of racemate

With 1-chloro-1-(dimethylamino)-2-methyl-1-propene; hydroxylamine hydrochloride; hydrogen; sodium acetate; triethylamine; In tetrahydrofuran; methanol; 5,5-dimethyl-1,3-cyclohexadiene; diethyl ether; ethanol; dichloromethane;

Reference yield:

: 33777-39-8
N-Phenacyldiallylamin

: tert-butyl (4aR,7aS)-2-benzamido-7a-phenyl-4,4a,5,7-tetrahydropyrrolo[3,4-d][1,3]thiazine-6-carboxylate

: 1463486-13-6
tert-butyl (4aS,7aR)-2-benzamido-7a-phenyl-4,4a,5,7-tetrahydropyrrolo[3,4-d][1,3]thiazine-6-carboxylate

Guidance literature:: Multi-step reaction with 8 steps

1: pyridine; hydroxylamine hydrochloride / ethanol / 4 h / 70 °C

2: toluene / 120 °C

3: 1,3-dimethylbarbituric acid; tetrakis(triphenylphosphine) palladium⁽⁰⁾ / chloroform / 18 h / Inert atmosphere

4: triethylamine / dichloromethane / 2 h

5: hydrogen / methanol / 20 °C / 760.05 Torr

6: tetrahydrofuran / 0 - 20 °C

7: 1-chloro-1-(dimethylamino)-2-methyl-1-propene / dichloromethane / 4 h / 0 - 20 °C / Inert atmosphere

8: SFC (Supercritical Fluid Chromatography) (Chiralpak AD / Resolution of racemate

With pyridine; tetrakis(triphenylphosphine) palladium⁽⁰⁾; 1,3-dimethylbarbituric acid; 1-chloro-1-(dimethylamino)-2-methyl-1-propene; hydroxylamine hydrochloride; hydrogen; triethylamine; In tetrahydrofuran; methanol; ethanol; dichloromethane; chloroform; toluene;