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

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Chemical Name:(1R,9aS)-7-bromo-3,3-dimethyl-1-(2-phenyl)ethyl-1-propyl-9,9a-dihydro-1H-[1,3]oxazolo[3,4-a]indole
CAS No.:849479-86-3
Molecular Formula:C₂₃H₂₈BrNO
Molecular Weight:414.385
Hs Code.:

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

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

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

There total 8 articles about (1R,9aS)-7-bromo-3,3-dimethyl-1-(2-phenyl)ethyl-1-propyl-9,9a-dihydro-1H-[1,3]oxazolo[3,4-a]indole 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: 72.0%

: 849479-85-2
(R)-3-((S)-5-Bromo-2,3-dihydro-1H-indol-2-yl)-1-phenyl-hexan-3-ol

: 77-76-9
2,2-dimethoxy-propane

: 849479-86-3
(1R,9aS)-7-bromo-3,3-dimethyl-1-(2-phenyl)ethyl-1-propyl-9,9a-dihydro-1H-[1,3]oxazolo[3,4-a]indole

Guidance literature:: With pyridinium p-toluenesulfonate; In dichloromethane; at 20 ℃; for 4h;
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

: 849479-86-3
(1R,9aS)-7-bromo-3,3-dimethyl-1-(2-phenyl)ethyl-1-propyl-9,9a-dihydro-1H-[1,3]oxazolo[3,4-a]indole

Guidance literature:: Multi-step reaction with 3 steps

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

2: 11 mg / TFA / CH₂Cl₂ / 3 h / 20 °C

3: 72 percent / pyridinium p-toluenesulfonate / CH₂Cl₂ / 4 h / 20 °C

With hydrogen; pyridinium p-toluenesulfonate; trifluoroacetic acid; palladium on activated charcoal; In dichloromethane; ethyl acetate;
DOI:10.1016/j.tet.2004.12.041

Reference yield:

: 79815-20-6,78348-24-0
(S)-indoline-2-carboxylic acid

: 849479-86-3
(1R,9aS)-7-bromo-3,3-dimethyl-1-(2-phenyl)ethyl-1-propyl-9,9a-dihydro-1H-[1,3]oxazolo[3,4-a]indole

Guidance literature:: Multi-step reaction with 9 steps

1: sulfuric acid / 6 h / 80 °C

2: 31.4 g / CH₂Cl₂ / 20 °C

3: 93 percent / NBS / dimethylformamide / 2 h / 0 °C

4: 83 percent / i-propylmagnesium chloride / tetrahydrofuran / 0.5 h / -10 °C

5: 25 percent / tetrahydrofuran; diethyl ether / 1.5 h / 0 °C

6: 85 percent / tetrahydrofuran; diethyl ether / 0.25 h / -78 °C

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

8: 11 mg / TFA / CH₂Cl₂ / 3 h / 20 °C

9: 72 percent / pyridinium p-toluenesulfonate / CH₂Cl₂ / 4 h / 20 °C

With N-Bromosuccinimide; sulfuric acid; hydrogen; isopropylmagnesium chloride; pyridinium p-toluenesulfonate; trifluoroacetic acid; palladium on activated charcoal; In tetrahydrofuran; diethyl ether; dichloromethane; ethyl acetate; N,N-dimethyl-formamide; 5: Grignard addition;
DOI:10.1016/j.tet.2004.12.041