(1R,2R,9aS)-1-(benzyloxy)-2-hydroxy-3(E)-isobutylidene-1-methyloctahydroquinolizine

Base Information

• Chemical Name: (1R,2R,9aS)-1-(benzyloxy)-2-hydroxy-3(E)-isobutylidene-1-methyloctahydroquinolizine
• CAS No.: 153108-76-0
• Molecular Formula: C₂₁H₃₁NO₂
• Molecular Weight: 329.483
• Mol file: 153108-76-0.mol

Synonyms:(1R,2R,9aS)-1-(benzyloxy)-2-hydroxy-3(E)-isobutylidene-1-methyloctahydroquinolizine

Chemical Property of (1R,2R,9aS)-1-(benzyloxy)-2-hydroxy-3(E)-isobutylidene-1-methyloctahydroquinolizine

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (1R,2R,9aS)-1-(benzyloxy)-2-hydroxy-3(E)-isobutylidene-1-methyloctahydroquinolizine

There total 14 articles about (1R,2R,9aS)-1-(benzyloxy)-2-hydroxy-3(E)-isobutylidene-1-methyloctahydroquinolizine 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%

(2S)-2-<(R)-1-(benzyloxy)-1-formylethyl>-N-<(E)-2-iodo-4-methyl-2-penten-1-yl>pipridine (153108-57-7) → (1R,2R,9aS)-1-(benzyloxy)-2-hydroxy-3(E)-isobutylidene-1-methyloctahydroquinolizine (153108-76-0)

Guidance literature:

With chromium dichloride; nickel dichloride; In N,N-dimethyl-formamide; for 20h; Ambient temperature;

Reference yield:

4-methyl-2-pentyn-1-ol (15787-92-5) → (1R,2R,9aS)-1-(benzyloxy)-2-hydroxy-3(E)-isobutylidene-1-methyloctahydroquinolizine (153108-76-0)

Guidance literature:

Multi-step reaction with 5 steps

1: 1.) PdCl₂-(PPh₃)2, 2.) Bu₃SnH, 3.) I₂

2: 96 percent / CBr₄, Ph₃P / CH₂Cl₂ / 0.17 h / 0 °C

3: 72 percent / i-Pr₂NEt / dimethylformamide / 48 h / Ambient temperature

4: 62 percent / BCl₃ / CH₂Cl₂ / 0.5 h / -78 °C

5: 53 percent / CrCl₂, NiCl₂ / dimethylformamide / 20 h / Ambient temperature

With chromium dichloride; bis-triphenylphosphine-palladium(II) chloride; carbon tetrabromide; iodine; tri-n-butyl-tin hydride; boron trichloride; N-ethyl-N,N-diisopropylamine; triphenylphosphine; nickel dichloride; In dichloromethane; N,N-dimethyl-formamide;

Reference yield:

(S)-(-)-1-(tert-butoxycarbonyl)-2-piperidinecarboxylic acid (26250-84-0) → (1R,2R,9aS)-1-(benzyloxy)-2-hydroxy-3(E)-isobutylidene-1-methyloctahydroquinolizine (153108-76-0)

Guidance literature:

Multi-step reaction with 11 steps

1: 94 percent / Ph₃P / acetonitrile / 1 h / Heating

2: 87 percent / tetrahydrofuran / 1.5 h / 0 °C

3: CH₂Cl₂ / 1 h / Ambient temperature

4: 1.) n-BuLi / 1.) hexane, THF, -30 deg C to -20 deg C, 1.5 h, 2.) hexane, THF, -78 deg C, 1 h

5: 76 percent / Hg(ClO₄)2*3H₂O / CHCl₃ / 3 h / Ambient temperature

6: 83 percent / i-Pr₂NEt / tetrahydrofuran / 2.5 h / Ambient temperature

7: 92 percent / KH / tetrahydrofuran / 1 h / Ambient temperature

8: 93 percent / AgNO₃ / ethanol / 1 h / Ambient temperature

9: 72 percent / i-Pr₂NEt / dimethylformamide / 48 h / Ambient temperature

10: 62 percent / BCl₃ / CH₂Cl₂ / 0.5 h / -78 °C

11: 53 percent / CrCl₂, NiCl₂ / dimethylformamide / 20 h / Ambient temperature

With chromium dichloride; n-butyllithium; mercury(II) perchlorate; boron trichloride; potassium hydride; silver nitrate; N-ethyl-N,N-diisopropylamine; triphenylphosphine; nickel dichloride; In tetrahydrofuran; ethanol; dichloromethane; chloroform; N,N-dimethyl-formamide; acetonitrile;

upstream raw materials:

(2S)-2-<(R)-1-(benzyloxy)-1-formylethyl>-N-<(E)-2-iodo-4-methyl-2-penten-1-yl>pipridine

4-methyl-2-pentyn-1-ol

(S)-(-)-1-(tert-butoxycarbonyl)-2-piperidinecarboxylic acid

(E)-2-iodo-4-methyl-2-penten-1-ol

Downstream raw materials:

Acetic acid (1R,2R,9aS)-1-benzyloxy-1-methyl-3-[2-methyl-prop-(E)-ylidene]-octahydro-quinolizin-2-yl ester