(1R,2S,8S,8aR)-octahydro-1,2,8-tris-(phenylmethoxy)indolizine

Base Information

Chemical Name:(1R,2S,8S,8aR)-octahydro-1,2,8-tris-(phenylmethoxy)indolizine
CAS No.:476171-66-1
Molecular Formula:C₂₉H₃₃NO₃
Molecular Weight:443.586
Hs Code.:

Synonyms:(1R,2S,8S,8aR)-octahydro-1,2,8-tris-(phenylmethoxy)indolizine

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Chemical Property of (1R,2S,8S,8aR)-octahydro-1,2,8-tris-(phenylmethoxy)indolizine

Chemical Property:

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Technology Process of (1R,2S,8S,8aR)-octahydro-1,2,8-tris-(phenylmethoxy)indolizine

There total 13 articles about (1R,2S,8S,8aR)-octahydro-1,2,8-tris-(phenylmethoxy)indolizine 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: 79.5%

: 476171-65-0
2R-(1'S-phenylmethoxy-4'-hydroxy)butyl-3R,4S-diphenylmethoxypyrrolidine

: 476171-66-1
(1R,2S,8S,8aR)-octahydro-1,2,8-tris-(phenylmethoxy)indolizine

Guidance literature:: 2R-(1'S-phenylmethoxy-4'-hydroxy)butyl-3R,4S-diphenylmethoxypyrrolidine; With carbon tetrabromide; triphenylphosphine; In dichloromethane; at 0 ℃; for 0.0833333h;

With triethylamine; In dichloromethane; at 4 ℃; for 20h; Further stages.;
DOI:10.1021/jo025977w

Reference yield:

: 5390-04-5
pent-1-yn-5-ol

: 476171-66-1
(1R,2S,8S,8aR)-octahydro-1,2,8-tris-(phenylmethoxy)indolizine

Guidance literature:: Multi-step reaction with 13 steps

1.1: 96 percent / imidazole / dimethylformamide / 3 h / 20 °C

2.1: n-BuLi / tetrahydrofuran / 0.12 h

2.2: 94.4 percent / tetrahydrofuran / 18 h / 20 °C

3.1: 99 percent / quinoline; H₂ / Pd/CaCO₃ / various solvent(s) / 0.5 h / 20 °C

4.1: 70.5 percent / tert-butyl hydroperoxide; D-(-)-diisopropyl tartrate; titanium(IV) isopropoxide / molecular sieves 4 Angstroem / CH₂Cl₂ / 4.5 h / -15 °C

5.1: oxalyl chloride; dimethyl sulfoxide; triethylamine / CH₂Cl₂ / -60 - 20 °C

6.1: KHMDS / toluene / 0.17 h

6.2: 82.2 percent / toluene / 0.5 h / 20 °C

7.1: 91.2 percent / p-toluenesulfonic acid monohydrate / 96 h / 110 °C

8.1: 95.4 percent / triethylamine / dimethylformamide / 18 h / 20 °C

9.1: 93.2 percent / benzylidene-bis(tricyclohexylphosphine)dichlororuthenium / CH₂Cl₂ / 20 h / Heating

10.1: 90.7 percent / K₂OsO₄*2H₂O; N-methylmorpholine N-oxide; water / acetone / 20 h / 20 °C

11.1: 85.5 percent / NaH; tetrabutylammonium iodide / tetrahydrofuran / 20 h / 20 °C

12.1: 85.2 percent / trifluoroacetic acid / 2 h / 20 °C

13.1: triphenylphosphine; carbon tetrabromide / CH₂Cl₂ / 0.08 h / 0 °C

13.2: 79.5 percent / triethylamine / CH₂Cl₂ / 20 h / 4 °C

With 1H-imidazole; quinoline; titanium(IV) isopropylate; tert.-butylhydroperoxide; potassium osmate(VI); n-butyllithium; oxalyl dichloride; carbon tetrabromide; water; hydrogen; tetra-(n-butyl)ammonium iodide; potassium hexamethylsilazane; sodium hydride; D-(-)-diisopropyl tartrate; toluene-4-sulfonic acid; dimethyl sulfoxide; 4-methylmorpholine N-oxide; triethylamine; triphenylphosphine; trifluoroacetic acid; Lindlar's catalyst; Grubbs catalyst first generation; 4 A molecular sieve; In tetrahydrofuran; dichloromethane; N,N-dimethyl-formamide; acetone; toluene; 4.1: Sharpless epoxidation / 5.1: Swern oxidation;
DOI:10.1021/jo025977w

Reference yield:

: 61362-77-4
5-[tert-butyldimethylsilyloxy]pent-1-yne

: 476171-66-1
(1R,2S,8S,8aR)-octahydro-1,2,8-tris-(phenylmethoxy)indolizine

Guidance literature:: Multi-step reaction with 12 steps

1.1: n-BuLi / tetrahydrofuran / 0.12 h

1.2: 94.4 percent / tetrahydrofuran / 18 h / 20 °C

2.1: 99 percent / quinoline; H₂ / Pd/CaCO₃ / various solvent(s) / 0.5 h / 20 °C

3.1: 70.5 percent / tert-butyl hydroperoxide; D-(-)-diisopropyl tartrate; titanium(IV) isopropoxide / molecular sieves 4 Angstroem / CH₂Cl₂ / 4.5 h / -15 °C

4.1: oxalyl chloride; dimethyl sulfoxide; triethylamine / CH₂Cl₂ / -60 - 20 °C

5.1: KHMDS / toluene / 0.17 h

5.2: 82.2 percent / toluene / 0.5 h / 20 °C

6.1: 91.2 percent / p-toluenesulfonic acid monohydrate / 96 h / 110 °C

7.1: 95.4 percent / triethylamine / dimethylformamide / 18 h / 20 °C

8.1: 93.2 percent / benzylidene-bis(tricyclohexylphosphine)dichlororuthenium / CH₂Cl₂ / 20 h / Heating

9.1: 90.7 percent / K₂OsO₄*2H₂O; N-methylmorpholine N-oxide; water / acetone / 20 h / 20 °C

10.1: 85.5 percent / NaH; tetrabutylammonium iodide / tetrahydrofuran / 20 h / 20 °C

11.1: 85.2 percent / trifluoroacetic acid / 2 h / 20 °C

12.1: triphenylphosphine; carbon tetrabromide / CH₂Cl₂ / 0.08 h / 0 °C

12.2: 79.5 percent / triethylamine / CH₂Cl₂ / 20 h / 4 °C

With quinoline; titanium(IV) isopropylate; tert.-butylhydroperoxide; potassium osmate(VI); n-butyllithium; oxalyl dichloride; carbon tetrabromide; water; hydrogen; tetra-(n-butyl)ammonium iodide; potassium hexamethylsilazane; sodium hydride; D-(-)-diisopropyl tartrate; toluene-4-sulfonic acid; dimethyl sulfoxide; 4-methylmorpholine N-oxide; triethylamine; triphenylphosphine; trifluoroacetic acid; Lindlar's catalyst; Grubbs catalyst first generation; 4 A molecular sieve; In tetrahydrofuran; dichloromethane; N,N-dimethyl-formamide; acetone; toluene; 3.1: Sharpless epoxidation / 4.1: Swern oxidation;
DOI:10.1021/jo025977w