(1S,2R,9R)-2-METHYL-OCTAHYDRO-2H-QUINOLIZIDINE-1-METHANOL

Base Information

• Chemical Name: (1S,2R,9R)-2-METHYL-OCTAHYDRO-2H-QUINOLIZIDINE-1-METHANOL
• CAS No.: 176210-35-8
• Molecular Formula: C₁₁H₂₁NO
• Molecular Weight: 183.294
• Mol file: 176210-35-8.mol

Synonyms:2H-Quinolizine-1-methanol,octahydro-2-methyl-, [1S-(1a,2b,9aa)]-

Chemical Property of (1S,2R,9R)-2-METHYL-OCTAHYDRO-2H-QUINOLIZIDINE-1-METHANOL

Chemical Property:

• PSA: 23.47000
• LogP: 1.42710

Purity/Quality:

97% ^*data from raw suppliers

(1S,2R,9R)-2-METHYL-OCTAHYDRO-2H-QUINOLIZIDINE-1-METHANOL 95.00% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of (1S,2R,9R)-2-METHYL-OCTAHYDRO-2H-QUINOLIZIDINE-1-METHANOL

There total 7 articles about (1S,2R,9R)-2-METHYL-OCTAHYDRO-2H-QUINOLIZIDINE-1-METHANOL 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: 67.0%

(1S,2R,9aR)-2-methyl-6-oxo-2,6,7,8,9,9a-hexahydro-1H-quinolizine-1-carbaldehyde (176210-30-3) → (1S,2R,9aR)-(2-methyloctahydroquinolizine-1-yl)methanol (176210-35-8)

Guidance literature:

(1S,2R,9aR)-2-methyl-6-oxo-2,6,7,8,9,9a-hexahydro-1H-quinolizine-1-carbaldehyde; With lithium aluminium tetrahydride; In diethyl ether; for 2h; Heating;

With sodium tetrahydroborate; In methanol; at 0 ℃; for 0.5h;

DOI:10.1016/S0040-4020(98)00490-6

Reference yield:

1-(4-chlorobutanoyl)-3-formyl-4(R)-methyl-1,4-dihydropyridine (176210-26-7) → (1S,2R,9aR)-(2-methyloctahydroquinolizine-1-yl)methanol (176210-35-8)

Guidance literature:

Multi-step reaction with 4 steps

1.1: NaI / acetone / 12 h / Heating

2.1: Zn; CuI; i-PrOH / H₂O; tetrahydrofuran / 2 h / ultrasonic conditions

3.1: 89 percent / Na₂CO₃ / methanol / 12 h / 20 °C

4.1: LiAlH₄ / diethyl ether / 2 h / Heating

4.2: 67 percent / NaBH₄ / methanol / 0.5 h / 0 °C

With copper(l) iodide; lithium aluminium tetrahydride; sodium carbonate; isopropyl alcohol; sodium iodide; zinc; In tetrahydrofuran; methanol; diethyl ether; water; acetone; 1.1: Iodination / 2.1: Cyclization / 3.1: Isomerization / 4.1: Reduction / 4.2: Reduction;

DOI:10.1016/S0040-4020(98)00490-6

Reference yield:

1-(4-iodobutanoyl)-3-formyl-4(R)-methyl-1,4-dihydropyridine (176210-28-9) → (1S,2R,9aR)-(2-methyloctahydroquinolizine-1-yl)methanol (176210-35-8)

Guidance literature:

Multi-step reaction with 3 steps

1.1: Zn; CuI; i-PrOH / H₂O; tetrahydrofuran / 2 h / ultrasonic conditions

2.1: 89 percent / Na₂CO₃ / methanol / 12 h / 20 °C

3.1: LiAlH₄ / diethyl ether / 2 h / Heating

3.2: 67 percent / NaBH₄ / methanol / 0.5 h / 0 °C

With copper(l) iodide; lithium aluminium tetrahydride; sodium carbonate; isopropyl alcohol; zinc; In tetrahydrofuran; methanol; diethyl ether; water; 1.1: Cyclization / 2.1: Isomerization / 3.1: Reduction / 3.2: Reduction;

DOI:10.1016/S0040-4020(98)00490-6

upstream raw materials:

(1S,2R,9aR)-2-methyl-6-oxo-2,6,7,8,9,9a-hexahydro-1H-quinolizine-1-carbaldehyde

1-(4-chlorobutanoyl)-3-formyl-4(R)-methyl-1,4-dihydropyridine

1-(4-iodobutanoyl)-3-formyl-4(R)-methyl-1,4-dihydropyridine

1-(4-chlorobutanoyl)-3-(1,3-dimethyl-4(S),5(S)-diphenylimidazolidin-2-yl)-4(R)-methyl-1,4-dihydropyridine