(3aS,9aR)-7-(benzyloxy)-5-methyl-1,2,3,3a,4,6,7,8,9,9a-decahydropyrrolo[1,2-a]quinoline

Base Information

• Chemical Name: (3aS,9aR)-7-(benzyloxy)-5-methyl-1,2,3,3a,4,6,7,8,9,9a-decahydropyrrolo[1,2-a]quinoline
• CAS No.: 1514903-46-8
• Molecular Formula: C₂₀H₂₇NO
• Molecular Weight: 297.44

Synonyms:(3aS,9aR)-7-(benzyloxy)-5-methyl-1,2,3,3a,4,6,7,8,9,9a-decahydropyrrolo[1,2-a]quinoline

Chemical Property of (3aS,9aR)-7-(benzyloxy)-5-methyl-1,2,3,3a,4,6,7,8,9,9a-decahydropyrrolo[1,2-a]quinoline

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Technology Process of (3aS,9aR)-7-(benzyloxy)-5-methyl-1,2,3,3a,4,6,7,8,9,9a-decahydropyrrolo[1,2-a]quinoline

There total 5 articles about (3aS,9aR)-7-(benzyloxy)-5-methyl-1,2,3,3a,4,6,7,8,9,9a-decahydropyrrolo[1,2-a]quinoline 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: 47.0%

4-(benzyloxy)cyclohexanone (2987-06-6) + tert-butyl (2S)-2-(2'-oxopropyl)pyrrolidine-1-carboxylate (1250851-46-7) → (3aS,9aR)-7-(benzyloxy)-5-methyl-1,2,3,3a,4,6,7,8,9,9a-decahydropyrrolo[1,2-a]quinoline (1514903-46-8) + (3aS,9aR)-7-(benzyloxy)-5-methyl-1,2,3,3a,4,6,7,8,9,9a-decahydropyrrolo[1,2-a]quinoline (1514903-73-1)

Guidance literature:

tert-butyl (2S)-2-(2'-oxopropyl)pyrrolidine-1-carboxylate; With trifluoroacetic acid; In dichloromethane; at 0 - 20 ℃; for 2h; Inert atmosphere;

4-(benzyloxy)cyclohexanone; With 2,2,2-trifluoroethyl trifluoromethanesulphonate; In tetrahydrofuran; at 20 ℃; for 72h; Inert atmosphere;

With sodium tetrahydroborate; In tetrahydrofuran; methanol; at 0 - 20 ℃; for 3h; diastereoselective reaction; Inert atmosphere;

DOI:10.1021/ol403229q

Reference yield:

(S)-tert-butyl 2-(2-(methoxy(methyl)amino)-2-oxoethyl)pyrrolidine-1-carboxylate (1034128-58-9) → (3aS,9aR)-7-(benzyloxy)-5-methyl-1,2,3,3a,4,6,7,8,9,9a-decahydropyrrolo[1,2-a]quinoline (1514903-46-8) + (3aS,9aR)-7-(benzyloxy)-5-methyl-1,2,3,3a,4,6,7,8,9,9a-decahydropyrrolo[1,2-a]quinoline (1514903-73-1)

Guidance literature:

Multi-step reaction with 2 steps

1.1: tetrahydrofuran / 0 - 20 °C / Inert atmosphere

2.1: trifluoroacetic acid / dichloromethane / 2 h / 0 - 20 °C / Inert atmosphere

2.2: 72 h / 20 °C / Inert atmosphere

2.3: 3 h / 0 - 20 °C / Inert atmosphere

With trifluoroacetic acid; In tetrahydrofuran; dichloromethane;

DOI:10.1021/ol403229q

Reference yield:

1-(tert-butoxycarbonyl)-L-proline (15761-39-4,59433-50-0) → (3aS,9aR)-7-(benzyloxy)-5-methyl-1,2,3,3a,4,6,7,8,9,9a-decahydropyrrolo[1,2-a]quinoline (1514903-46-8) + (3aS,9aR)-7-(benzyloxy)-5-methyl-1,2,3,3a,4,6,7,8,9,9a-decahydropyrrolo[1,2-a]quinoline (1514903-73-1)

Guidance literature:

Multi-step reaction with 5 steps

1.1: isobutyl chloroformate; triethylamine / tetrahydrofuran / 0.5 h / 0 °C / Inert atmosphere

1.2: Inert atmosphere

2.1: silver benzoate / 3 h / 0 - 20 °C / Inert atmosphere

3.1: isopropylmagnesium chloride / tetrahydrofuran / 4.5 h / -20 - -8 °C / Inert atmosphere

4.1: tetrahydrofuran / 0 - 20 °C / Inert atmosphere

5.1: trifluoroacetic acid / dichloromethane / 2 h / 0 - 20 °C / Inert atmosphere

5.2: 72 h / 20 °C / Inert atmosphere

5.3: 3 h / 0 - 20 °C / Inert atmosphere

With isopropylmagnesium chloride; silver benzoate; triethylamine; trifluoroacetic acid; isobutyl chloroformate; In tetrahydrofuran; dichloromethane;

DOI:10.1021/ol403229q

upstream raw materials:

4-(benzyloxy)cyclohexanone

tert-butyl (2S)-2-(2'-oxopropyl)pyrrolidine-1-carboxylate

(S)-tert-butyl 2-(2-(methoxy(methyl)amino)-2-oxoethyl)pyrrolidine-1-carboxylate

1-(tert-butoxycarbonyl)-L-proline

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