(8S,8aS)-8-hydroxy-8-methyl-6(Z)-<4-(benzyloxy)-2(R)-methylbutylidene>octahydroindolizidine

Base Information

Chemical Name:(8S,8aS)-8-hydroxy-8-methyl-6(Z)-<4-(benzyloxy)-2(R)-methylbutylidene>octahydroindolizidine
CAS No.:90246-45-0
Molecular Formula:C₂₁H₃₁NO₂
Molecular Weight:329.483
Hs Code.:

Synonyms:(8S,8aS)-8-hydroxy-8-methyl-6(Z)-<4-(benzyloxy)-2(R)-methylbutylidene>octahydroindolizidine

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Chemical Property of (8S,8aS)-8-hydroxy-8-methyl-6(Z)-<4-(benzyloxy)-2(R)-methylbutylidene>octahydroindolizidine

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Technology Process of (8S,8aS)-8-hydroxy-8-methyl-6(Z)-<4-(benzyloxy)-2(R)-methylbutylidene>octahydroindolizidine

There total 17 articles about (8S,8aS)-8-hydroxy-8-methyl-6(Z)-<4-(benzyloxy)-2(R)-methylbutylidene>octahydroindolizidine 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: 52.0%

: 90246-46-1
(1S,7aS)-1-((Z)-(R)-6-Benzyloxy-4-methyl-2-trimethylsilanyl-hex-2-enyl)-1-methyl-tetrahydro-pyrrolo[1,2-c]oxazole

: 90246-45-0
(8S,8aS)-8-hydroxy-8-methyl-6(Z)-<4-(benzyloxy)-2(R)-methylbutylidene>octahydroindolizidine

Guidance literature:: With formaldehyd; camphor-10-sulfonic acid; In acetonitrile; at 80 ℃; for 13h;
DOI:10.1021/ja00327a022

Reference yield:

: chloroformate ester of 5-(benzyloxy)-1-pentyn-3-ol

: 90246-45-0
(8S,8aS)-8-hydroxy-8-methyl-6(Z)-<4-(benzyloxy)-2(R)-methylbutylidene>octahydroindolizidine

Guidance literature:: Multi-step reaction with 9 steps

1: 37 percent

2: 67 percent / Cl₃SiH

3: 65 percent / diethyl ether / 0.5 h / Heating

4: 85 percent / 4-(dimethylamino)pyridine, pyridine

5: 1) CuI / 1) ether, 2) THF, 23 deg C, 10 min

6: 1) i-Bu₂AlH, MeLi / 1) hexane, THF, 23 deg C, 0.5+0.5 h, 2) THF, 60 deg C, 25 h

7: KOH / ethanol / 12 h / 90 °C

8: 496 mg / H₂O; methanol / 4 h / 23 °C

9: 52 percent / paraformaldehyde, camphorsulfonic acid / acetonitrile / 13 h / 80 °C

With pyridine; dmap; potassium hydroxide; copper(l) iodide; formaldehyd; camphor-10-sulfonic acid; trichlorosilane; methyllithium; diisobutylaluminium hydride; In methanol; diethyl ether; ethanol; water; acetonitrile;
DOI:10.1021/ja00327a022

Reference yield:

: 51207-68-2
(2S)-N-Benzyloxycarbony-2-(1'-hydroxy-1'-methylethyl)pyrrolidine

: 90246-45-0
(8S,8aS)-8-hydroxy-8-methyl-6(Z)-<4-(benzyloxy)-2(R)-methylbutylidene>octahydroindolizidine

Guidance literature:: Multi-step reaction with 6 steps

1: SOCl₂, Et₃N / tetrahydrofuran / 0.5 h / -50 - -45 °C

2: 37 percent / m-chloroperbenzoic acid / CH₂Cl₂ / 3 h / 25 °C

3: 1) i-Bu₂AlH, MeLi / 1) hexane, THF, 23 deg C, 0.5+0.5 h, 2) THF, 60 deg C, 25 h

4: KOH / ethanol / 12 h / 90 °C

5: 496 mg / H₂O; methanol / 4 h / 23 °C

6: 52 percent / paraformaldehyde, camphorsulfonic acid / acetonitrile / 13 h / 80 °C

With potassium hydroxide; formaldehyd; thionyl chloride; camphor-10-sulfonic acid; methyllithium; diisobutylaluminium hydride; triethylamine; 3-chloro-benzenecarboperoxoic acid; In tetrahydrofuran; methanol; ethanol; dichloromethane; water; acetonitrile;
DOI:10.1021/ja00327a022