(1R,9aS)-3,3-dimethyl-1-(2-phenyl)ethyl-1-propyl-9,9a-dihydro-1H-[1,3]oxazolo[3,4-a]indole-7-carboxylic acid allyl ester

Base Information

Chemical Name:(1R,9aS)-3,3-dimethyl-1-(2-phenyl)ethyl-1-propyl-9,9a-dihydro-1H-[1,3]oxazolo[3,4-a]indole-7-carboxylic acid allyl ester
CAS No.:849480-38-2
Molecular Formula:C₂₇H₃₃NO₃
Molecular Weight:419.564
Hs Code.:

Synonyms:(1R,9aS)-3,3-dimethyl-1-(2-phenyl)ethyl-1-propyl-9,9a-dihydro-1H-[1,3]oxazolo[3,4-a]indole-7-carboxylic acid allyl ester

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Chemical Property of (1R,9aS)-3,3-dimethyl-1-(2-phenyl)ethyl-1-propyl-9,9a-dihydro-1H-[1,3]oxazolo[3,4-a]indole-7-carboxylic acid allyl ester

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Technology Process of (1R,9aS)-3,3-dimethyl-1-(2-phenyl)ethyl-1-propyl-9,9a-dihydro-1H-[1,3]oxazolo[3,4-a]indole-7-carboxylic acid allyl ester

There total 11 articles about (1R,9aS)-3,3-dimethyl-1-(2-phenyl)ethyl-1-propyl-9,9a-dihydro-1H-[1,3]oxazolo[3,4-a]indole-7-carboxylic acid allyl 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: 89.0%

: 849480-37-1
3,3-dimethyl-1-phenethyl-1-propyl-9,9a-dihydro-1H-oxazolo[3,4-a]indole-7-carboxylic acid

: 106-95-6
allyl bromide

: 849480-38-2
(1R,9aS)-3,3-dimethyl-1-(2-phenyl)ethyl-1-propyl-9,9a-dihydro-1H-[1,3]oxazolo[3,4-a]indole-7-carboxylic acid allyl ester

Guidance literature:: With potassium carbonate; In N,N-dimethyl-formamide; at 20 ℃; for 2h;
DOI:10.1016/j.tet.2004.12.041

Reference yield:

: 849479-91-0
tert-butyl (2S)-5-bromo-2-butyrylindoline-1-carboxylate

: 849480-38-2
(1R,9aS)-3,3-dimethyl-1-(2-phenyl)ethyl-1-propyl-9,9a-dihydro-1H-[1,3]oxazolo[3,4-a]indole-7-carboxylic acid allyl ester

Guidance literature:: Multi-step reaction with 6 steps

1.1: 85 percent / tetrahydrofuran; diethyl ether / 0.25 h / -78 °C

2.1: H₂ / Pd/C / ethyl acetate / 24 h / 20 °C

3.1: 11 mg / TFA / CH₂Cl₂ / 3 h / 20 °C

4.1: 72 percent / pyridinium p-toluenesulfonate / CH₂Cl₂ / 4 h / 20 °C

5.1: t-BuLi / diethyl ether; pentane / 0.25 h / -78 °C

5.2: 87 percent / diethyl ether; pentane / -78 - 0 °C

6.1: 89 percent / K₂CO₃ / dimethylformamide / 2 h / 20 °C

With hydrogen; tert.-butyl lithium; pyridinium p-toluenesulfonate; potassium carbonate; trifluoroacetic acid; palladium on activated charcoal; In tetrahydrofuran; diethyl ether; dichloromethane; ethyl acetate; N,N-dimethyl-formamide; pentane;
DOI:10.1016/j.tet.2004.12.041

Reference yield:

: 849479-97-6
tert-butyl (2S)-5-bromo-2-[(1R)-1-hydroxy-1-phenylethynyl-1-butyl]indoline-1-carboxylate

: 849480-38-2
(1R,9aS)-3,3-dimethyl-1-(2-phenyl)ethyl-1-propyl-9,9a-dihydro-1H-[1,3]oxazolo[3,4-a]indole-7-carboxylic acid allyl ester

Guidance literature:: Multi-step reaction with 5 steps

1.1: H₂ / Pd/C / ethyl acetate / 24 h / 20 °C

2.1: 11 mg / TFA / CH₂Cl₂ / 3 h / 20 °C

3.1: 72 percent / pyridinium p-toluenesulfonate / CH₂Cl₂ / 4 h / 20 °C

4.1: t-BuLi / diethyl ether; pentane / 0.25 h / -78 °C

4.2: 87 percent / diethyl ether; pentane / -78 - 0 °C

5.1: 89 percent / K₂CO₃ / dimethylformamide / 2 h / 20 °C

With hydrogen; tert.-butyl lithium; pyridinium p-toluenesulfonate; potassium carbonate; trifluoroacetic acid; palladium on activated charcoal; In diethyl ether; dichloromethane; ethyl acetate; N,N-dimethyl-formamide; pentane;
DOI:10.1016/j.tet.2004.12.041