(3aα,6α,6aβ,10α,10aβ,10bα)-(+/-)-Octahydro-6a-methyl-10a-<3-(phenylmethoxy)propyl>-1H-3a,10,6-(nitrilomethano)benzazulene-5,8(4H,6H)-dione

Base Information

Chemical Name:(3aα,6α,6aβ,10α,10aβ,10bα)-(+/-)-Octahydro-6a-methyl-10a-<3-(phenylmethoxy)propyl>-1H-3a,10,6-(nitrilomethano)benzazulene-5,8(4H,6H)-dione
CAS No.:138489-34-6
Molecular Formula:C₂₆H₃₃NO₃
Molecular Weight:407.553
Hs Code.:

(3aα,6α,6aβ,10α,10aβ,10bα)-(+/-)-Octahydro-6a-methyl-10a-<3-(phenylmethoxy)propyl>-1H-3a,10,6-(nitrilomethano)benz<e>azulene-5,8(4H,6H)-dione

Synonyms:(3aα,6α,6aβ,10α,10aβ,10bα)-(+/-)-Octahydro-6a-methyl-10a-<3-(phenylmethoxy)propyl>-1H-3a,10,6-(nitrilomethano)benzazulene-5,8(4H,6H)-dione

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Chemical Property of (3aα,6α,6aβ,10α,10aβ,10bα)-(+/-)-Octahydro-6a-methyl-10a-<3-(phenylmethoxy)propyl>-1H-3a,10,6-(nitrilomethano)benzazulene-5,8(4H,6H)-dione

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Technology Process of (3aα,6α,6aβ,10α,10aβ,10bα)-(+/-)-Octahydro-6a-methyl-10a-<3-(phenylmethoxy)propyl>-1H-3a,10,6-(nitrilomethano)benzazulene-5,8(4H,6H)-dione

There total 16 articles about (3aα,6α,6aβ,10α,10aβ,10bα)-(+/-)-Octahydro-6a-methyl-10a-<3-(phenylmethoxy)propyl>-1H-3a,10,6-(nitrilomethano)benzazulene-5,8(4H,6H)-dione 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: 70.0%

: 138489-33-5
(3aα,4α,7aβ,10aβ,10bα,10cα)-(+/-)-3a,4,5,6,8,9,10,10a,10b,10c-Decahydro-4-hydroxy-1-methyl-10b-<3-(phenylmethoxy)propyl>4,7a-methano-3H,7aH-cyclopenta<4,5>pyrrolo<3,2,1-ij>quinolin-3-one

: 138489-34-6
(3aα,6α,6aβ,10α,10aβ,10bα)-(+/-)-Octahydro-6a-methyl-10a-<3-(phenylmethoxy)propyl>-1H-3a,10,6-(nitrilomethano)benzazulene-5,8(4H,6H)-dione

Guidance literature:: With sodium methylate; In methanol; for 8h;
DOI:10.1021/jo00035a007

Reference yield:

: 104115-44-8,1460-38-4
(2-oxocyclopent)acetic acid

: 138489-34-6
(3aα,6α,6aβ,10α,10aβ,10bα)-(+/-)-Octahydro-6a-methyl-10a-<3-(phenylmethoxy)propyl>-1H-3a,10,6-(nitrilomethano)benzazulene-5,8(4H,6H)-dione

Guidance literature:: Multi-step reaction with 13 steps

1: 1) ethyl chloroformate, NEt₃ / 1) THF, -30 deg C, 2 h, 2) -10 deg C to r.t. overnight

2: 83 percent / p-toluenesulfonic acid monohydrate / toluene / 18 h / Heating

3: 1) lithium diisopropylamide / 1) THF, hexane, 0 deg C, 1 h, 2) 0 deg C to r.t. overnight

4: 1) Lawesson's reagent, 2) 1M HCl / 1) THF, ultrasound, 0 deg C to r.t. over 1.5 h then 6.5 h, 2) MeOH, acetone, r.t., 45 min

5: pyridinium p-toluenesulfonate / benzene / 7 h / Heating

6: 1) lithium diisopropylamide / 1) THF, hexane, 0 deg C, 30 min, 2) 10 min

7: 1) triethyloxonium tetrafluoroborate, b) 2,6-di-tert-butylpyridine, 2) NEt₃ / 1) CHCl₃, r.t., 170 min, b) 110 min, 2) CHCl₃, reflux, 46 h

8: 1) 2,6-di-tert-butylpyridine, 2) NaBH₄ / 1) CH₂Cl₂, 0 deg C, 2) MeOH, -25 deg C

9: 10percent HCl, HOAc / diethyl ether / 168 h / 0 - 5 °C

10: 1) lithium 2,2,6,6-tetramethylpiperidide / 1) THF, hexane, -78 deg C, 165 min, 2) THF, 45 min

11: m-chloroperoxybenzoic acid / CH₂Cl₂; methanol / a) -78 deg C to -20 deg C over 1 h, b) -30 to -10 deg C, 1 h

12: HCl, H₂SO₄ / acetone / 8 h / Ambient temperature

13: 70 percent / NaOMe / methanol / 8 h

With Lawessons reagent; hydrogenchloride; sodium tetrahydroborate; 2,6-di-tert-butyl-pyridine; sulfuric acid; 2,2,6,6-tetramethylpiperidinyl-lithium; sodium methylate; triethyloxonium fluoroborate; pyridinium p-toluenesulfonate; chloroformic acid ethyl ester; toluene-4-sulfonic acid; acetic acid; triethylamine; 3-chloro-benzenecarboperoxoic acid; lithium diisopropyl amide; In methanol; diethyl ether; dichloromethane; acetone; toluene; benzene;
DOI:10.1021/jo00035a007

Reference yield:

: 138489-23-3
(3aS,6aR)-6a-Chloro-hexahydro-cyclopenta[b]furan-2-one

: 138489-34-6
(3aα,6α,6aβ,10α,10aβ,10bα)-(+/-)-Octahydro-6a-methyl-10a-<3-(phenylmethoxy)propyl>-1H-3a,10,6-(nitrilomethano)benzazulene-5,8(4H,6H)-dione

Guidance literature:: Multi-step reaction with 13 steps

1: 71 percent / K₂CO₃ / tetrahydrofuran

2: p-toluenesulfonic acid / toluene / Heating

3: 1) lithium diisopropylamide / 1) THF, hexane, 0 deg C, 1 h, 2) 0 deg C to r.t. overnight

4: 1) Lawesson's reagent, 2) 1M HCl / 1) THF, ultrasound, 0 deg C to r.t. over 1.5 h then 6.5 h, 2) MeOH, acetone, r.t., 45 min

5: pyridinium p-toluenesulfonate / benzene / 7 h / Heating

6: 1) lithium diisopropylamide / 1) THF, hexane, 0 deg C, 30 min, 2) 10 min

7: 1) triethyloxonium tetrafluoroborate, b) 2,6-di-tert-butylpyridine, 2) NEt₃ / 1) CHCl₃, r.t., 170 min, b) 110 min, 2) CHCl₃, reflux, 46 h

8: 1) 2,6-di-tert-butylpyridine, 2) NaBH₄ / 1) CH₂Cl₂, 0 deg C, 2) MeOH, -25 deg C

9: 10percent HCl, HOAc / diethyl ether / 168 h / 0 - 5 °C

10: 1) lithium 2,2,6,6-tetramethylpiperidide / 1) THF, hexane, -78 deg C, 165 min, 2) THF, 45 min

11: m-chloroperoxybenzoic acid / CH₂Cl₂; methanol / a) -78 deg C to -20 deg C over 1 h, b) -30 to -10 deg C, 1 h

12: HCl, H₂SO₄ / acetone / 8 h / Ambient temperature

13: 70 percent / NaOMe / methanol / 8 h

With Lawessons reagent; hydrogenchloride; sodium tetrahydroborate; 2,6-di-tert-butyl-pyridine; sulfuric acid; 2,2,6,6-tetramethylpiperidinyl-lithium; sodium methylate; triethyloxonium fluoroborate; pyridinium p-toluenesulfonate; potassium carbonate; toluene-4-sulfonic acid; acetic acid; triethylamine; 3-chloro-benzenecarboperoxoic acid; lithium diisopropyl amide; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; acetone; toluene; benzene;
DOI:10.1021/jo00035a007