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

Base Information

• Chemical Name: (1S,2R,8R,8aR)-octahydro-8-hydroxy-1,2-bis(phenylmethoxy)indolizine
• CAS No.: 130412-86-1
• Molecular Formula: C₂₂H₂₇NO₃
• Molecular Weight: 353.461
• Mol file: 130412-86-1.mol

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

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

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

There total 12 articles about (1S,2R,8R,8aR)-octahydro-8-hydroxy-1,2-bis(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: 75.8%

(1S,2R,8R,8aS)-octahydro-1,2-bis(phenylmethoxy)-8-[[(1,1-dimethylethyl)diphenylsilyl]oxy]-indolizine (774611-15-3) → (1S,2R,8R,8aR)-octahydro-8-hydroxy-1,2-bis(phenylmethoxy)indolizine (130412-86-1)

Guidance literature:

With tetrabutyl ammonium fluoride; In tetrahydrofuran; at 20 ℃; for 120h;

DOI:10.1071/CH04009

Reference yield:

(2R,3S)-2-[3-(4-Methoxy-benzyloxy)-propyl]-3-vinyl-oxirane → (1S,2R,8R,8aR)-octahydro-8-hydroxy-1,2-bis(phenylmethoxy)indolizine (130412-86-1)

Guidance literature:

Multi-step reaction with 10 steps

1: 88 percent / LiOTf / 1 h / 110 °C / microwave irradiation

2: 77 percent / Et₃N / CH₂Cl₂ / 2 h / 0 °C

3: 77 percent / (benzylidene)bis(tricyclohexylphosphine)dichlororuthenium / CH₂Cl₂ / 18 h / Heating

4: K₂OsO₄*2H₂O; N-methylmorpholine oxide; pyridine / acetone; H₂O / 168 h / 20 °C

5: 100 percent / NaH; tetrabutylammonium iodide / tetrahydrofuran / 48 h / 20 °C

6: 83.7 percent / NaOH / methanol; H₂O / 2 h / 110 °C / microwave irradiation

7: 96.9 percent / imidazole / acetonitrile / 72 h / 65 °C

8: 91.8 percent / cerium(IV) ammonium nitrate / acetonitrile; H₂O / 3 h / 20 °C

9: 93.4 percent / CBr₄; PPh₃; Et₃N / CH₂Cl₂ / 0 - 4 °C

10: 75.8 percent / tetra-n-butylammonium fluoride / tetrahydrofuran / 120 h / 20 °C

With pyridine; 1H-imidazole; sodium hydroxide; potassium osmate(VI); Grubbs catalyst first generation; ammonium cerium(IV) nitrate; carbon tetrabromide; tetrabutyl ammonium fluoride; tetra-(n-butyl)ammonium iodide; sodium hydride; lithium trifluoromethanesulfonate; 4-methylmorpholine N-oxide; triethylamine; triphenylphosphine; In tetrahydrofuran; methanol; dichloromethane; water; acetone; acetonitrile;

DOI:10.1071/CH04009

Reference yield:

7-[(4-methoxyphenyl)methoxy]-(4R)-hydroxy-(3S)-allylaminohept-1-ene (476171-47-8) → (1S,2R,8R,8aR)-octahydro-8-hydroxy-1,2-bis(phenylmethoxy)indolizine (130412-86-1)

Guidance literature:

Multi-step reaction with 9 steps

1: 77 percent / Et₃N / CH₂Cl₂ / 2 h / 0 °C

2: 77 percent / (benzylidene)bis(tricyclohexylphosphine)dichlororuthenium / CH₂Cl₂ / 18 h / Heating

3: K₂OsO₄*2H₂O; N-methylmorpholine oxide; pyridine / acetone; H₂O / 168 h / 20 °C

4: 100 percent / NaH; tetrabutylammonium iodide / tetrahydrofuran / 48 h / 20 °C

5: 83.7 percent / NaOH / methanol; H₂O / 2 h / 110 °C / microwave irradiation

6: 96.9 percent / imidazole / acetonitrile / 72 h / 65 °C

7: 91.8 percent / cerium(IV) ammonium nitrate / acetonitrile; H₂O / 3 h / 20 °C

8: 93.4 percent / CBr₄; PPh₃; Et₃N / CH₂Cl₂ / 0 - 4 °C

9: 75.8 percent / tetra-n-butylammonium fluoride / tetrahydrofuran / 120 h / 20 °C

With pyridine; 1H-imidazole; sodium hydroxide; potassium osmate(VI); Grubbs catalyst first generation; ammonium cerium(IV) nitrate; carbon tetrabromide; tetrabutyl ammonium fluoride; tetra-(n-butyl)ammonium iodide; sodium hydride; 4-methylmorpholine N-oxide; triethylamine; triphenylphosphine; In tetrahydrofuran; methanol; dichloromethane; water; acetone; acetonitrile;

DOI:10.1071/CH04009

upstream raw materials:

(1S,2R,8R,8aS)-octahydro-1,2-bis(phenylmethoxy)-8-[[(1,1-dimethylethyl)diphenylsilyl]oxy]-indolizine

(1R,6R,7S,7aS)-1-[3-[(4-methoxyphenyl)methoxy]propyl]-tetrahydro-6,7-dihydroxy-1H,3H-pyrrolo[1,2-c]oxazol-3-one

(2R,3S,4R)-2-[(1R)-1-hydroxy-4-[(4-methoxyphenyl)methoxy]butyl]-3,4-bis(phenylmethoxy)pyrrolidine

(1R,6R,7S,7aR)-tetrahydro-1-[3-[(4-methoxyphenyl)methoxy]propyl]-6,7-bis(phenylmethoxy)-1H,3H-pyrrolo[1,2-c]oxazol-3-one

Downstream raw materials:

swainsonine

Refernces