(3aS,6R,7aR*)-N-benzyl-3a-<3,4-(methylenedioxy)phenyl>-6-<(tert-butyldimethylsilyl)oxy>-2,3,3a,6,7,7a-hexahydro-1H-indole

Base Information

Chemical Name:(3aS*,6R*,7aR*)-N-benzyl-3a-<3,4-(methylenedioxy)phenyl>-6-<(tert-butyldimethylsilyl)oxy>-2,3,3a,6,7,7a-hexahydro-1H-indole
CAS No.:114635-87-9
Molecular Formula:C₂₈H₃₇NO₃Si
Molecular Weight:463.692
Hs Code.:

Synonyms:(3aS*,6R*,7aR*)-N-benzyl-3a-<3,4-(methylenedioxy)phenyl>-6-<(tert-butyldimethylsilyl)oxy>-2,3,3a,6,7,7a-hexahydro-1H-indole

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Chemical Property of (3aS*,6R*,7aR*)-N-benzyl-3a-<3,4-(methylenedioxy)phenyl>-6-<(tert-butyldimethylsilyl)oxy>-2,3,3a,6,7,7a-hexahydro-1H-indole

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Technology Process of (3aS*,6R*,7aR*)-N-benzyl-3a-<3,4-(methylenedioxy)phenyl>-6-<(tert-butyldimethylsilyl)oxy>-2,3,3a,6,7,7a-hexahydro-1H-indole

There total 6 articles about (3aS*,6R*,7aR*)-N-benzyl-3a-<3,4-(methylenedioxy)phenyl>-6-<(tert-butyldimethylsilyl)oxy>-2,3,3a,6,7,7a-hexahydro-1H-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: 94.0%

: 69739-34-0
t-butyldimethylsiyl triflate

: 111923-08-1
(3aS*,6R*,7aR*)-N-benzyl-3a-<3,4-(methylenedioxy)phenyl>-6-hydroxy-2,3,3a,6,7,7a-hexahydro-1H-indole

: 114635-87-9
(3aS*,6R*,7aR*)-N-benzyl-3a-<3,4-(methylenedioxy)phenyl>-6-<(tert-butyldimethylsilyl)oxy>-2,3,3a,6,7,7a-hexahydro-1H-indole

Guidance literature:: With N-ethyl-N,N-diisopropylamine; In dichloromethane; at 0 ℃; for 0.75h;
DOI:10.1021/jo00249a011

Reference yield:

: 111923-07-0
(3aS*,7aR*)-N-benzyl-3a-<3,4-(methylenedioxy)phenyl>-2,3,3a,6,7,7a-hexahydro-1H-indol-6-one

: 114635-87-9
(3aS*,6R*,7aR*)-N-benzyl-3a-<3,4-(methylenedioxy)phenyl>-6-<(tert-butyldimethylsilyl)oxy>-2,3,3a,6,7,7a-hexahydro-1H-indole

Guidance literature:: Multi-step reaction with 5 steps

1: 31 percent / AlH₃ / tetrahydrofuran / 2 h / 0 °C

2: Et₃N / tetrahydrofuran / 0.5 h / 0 °C

3: dimethylformamide / 40 h / Ambient temperature

4: K₂CO₃ / methanol / 2 h / Ambient temperature

5: 94 percent / diisopropylethylamine / CH₂Cl₂ / 0.75 h / 0 °C

With aluminium hydride; potassium carbonate; triethylamine; N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; methanol; dichloromethane; N,N-dimethyl-formamide;
DOI:10.1021/jo00249a011

Reference yield:

: 111923-06-9
4-<2-<<(allyloxy)carbonyl>benzylamino>ethyl>-4-<3,4-(methylenedioxy)phenyl>cyclohexadienone

: 114635-87-9
(3aS*,6R*,7aR*)-N-benzyl-3a-<3,4-(methylenedioxy)phenyl>-6-<(tert-butyldimethylsilyl)oxy>-2,3,3a,6,7,7a-hexahydro-1H-indole

Guidance literature:: Multi-step reaction with 6 steps

1: 87 percent / 2-ethylhexanoic acid, Pd(PPh₃)4, Ph₃P / CH₂Cl₂ / 24 h / Ambient temperature

2: 31 percent / AlH₃ / tetrahydrofuran / 2 h / 0 °C

3: Et₃N / tetrahydrofuran / 0.5 h / 0 °C

4: dimethylformamide / 40 h / Ambient temperature

5: K₂CO₃ / methanol / 2 h / Ambient temperature

6: 94 percent / diisopropylethylamine / CH₂Cl₂ / 0.75 h / 0 °C

With aluminium hydride; tetrakis(triphenylphosphine) palladium⁽⁰⁾; 2-Ethylhexanoic acid; potassium carbonate; triethylamine; N-ethyl-N,N-diisopropylamine; triphenylphosphine; In tetrahydrofuran; methanol; dichloromethane; N,N-dimethyl-formamide;
DOI:10.1021/jo00249a011