(3aS,4S,5R)-N-(piperonyloyl)-4,5-epoxy-5,6-dihydro-4H-3a-(benzyloxycarbonyl)indoline

Base Information

Chemical Name:(3aS,4S,5R)-N-(piperonyloyl)-4,5-epoxy-5,6-dihydro-4H-3a-(benzyloxycarbonyl)indoline
CAS No.:178449-44-0
Molecular Formula:C₂₄H₂₁NO₆
Molecular Weight:419.434
Hs Code.:

Synonyms:(3aS,4S,5R)-N-(piperonyloyl)-4,5-epoxy-5,6-dihydro-4H-3a-(benzyloxycarbonyl)indoline

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Chemical Property of (3aS,4S,5R)-N-(piperonyloyl)-4,5-epoxy-5,6-dihydro-4H-3a-(benzyloxycarbonyl)indoline

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Technology Process of (3aS,4S,5R)-N-(piperonyloyl)-4,5-epoxy-5,6-dihydro-4H-3a-(benzyloxycarbonyl)indoline

There total 10 articles about (3aS,4S,5R)-N-(piperonyloyl)-4,5-epoxy-5,6-dihydro-4H-3a-(benzyloxycarbonyl)indoline 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: 53.0%

: (3aS,4S,5R)-N-(6-bromopiperonyloyl)-4,5-epoxy-5,6-dihydro-4H-3a-(benzyloxycarbonyl)indoline

: 178449-44-0
(3aS,4S,5R)-N-(piperonyloyl)-4,5-epoxy-5,6-dihydro-4H-3a-(benzyloxycarbonyl)indoline

: 151071-66-8
(2R,3S,12S,15R,16R)-2,3-epoxy-12-(benzyloxycarbonyl)-9,10-galanthan-7-one

Guidance literature:: With 2,2'-azobis(isobutyronitrile); tri-n-butyl-tin hydride; In benzene; Heating;

Reference yield: 51.0%

: 178449-43-9
(1aR,6aS,6bS)-4-(6-Iodo-benzo[1,3]dioxole-5-carbonyl)-1a,2,4,5,6,6b-hexahydro-1-oxa-4-aza-cyclopropa[e]indene-6a-carboxylic acid benzyl ester

: 178449-44-0
(3aS,4S,5R)-N-(piperonyloyl)-4,5-epoxy-5,6-dihydro-4H-3a-(benzyloxycarbonyl)indoline

: 151071-66-8
(2R,3S,12S,15R,16R)-2,3-epoxy-12-(benzyloxycarbonyl)-9,10-galanthan-7-one

Guidance literature:: With 2,2'-azobis(isobutyronitrile); tri-n-butyl-tin hydride; In benzene; for 5h; Heating;
DOI:10.1021/ja9606440

Reference yield:

: 151071-70-4
(2'S,6R)-1-methoxy-6-(2-azidoethyl)-6-<<2'-(methoxymethyl)pyrrolidinyl>carbonyl>-1,4-cyclohexadiene

: 178449-44-0
(3aS,4S,5R)-N-(piperonyloyl)-4,5-epoxy-5,6-dihydro-4H-3a-(benzyloxycarbonyl)indoline

Guidance literature:: Multi-step reaction with 6 steps

1: 95 percent / aq. 6M HCl / methanol

2: 82 percent / I₂, H₂O / tetrahydrofuran / 12 h

3: 90 percent / Ph₃P / tetrahydrofuran / 9 h / Heating

4: 98 percent / Et₃N / CH₂Cl₂ / 12 h / 0 - 20 °C

5: 1.) n-BuLi / 1.) THF, hexane, -78 deg C, 5 min, 2.) THF, hexane, from -78 deg C to RT, 5 h

6: 45 percent / Bu₃SnH, AIBN / benzene / 16 h / Heating

With hydrogenchloride; n-butyllithium; 2,2'-azobis(isobutyronitrile); water; iodine; tri-n-butyl-tin hydride; triethylamine; triphenylphosphine; In tetrahydrofuran; methanol; dichloromethane; benzene;
DOI:10.1021/ja9606440