6-hydroxy-2-methyl-4a-phenyl-cis-decahydroisoquinoline

Base Information

• Chemical Name: 6-hydroxy-2-methyl-4a-phenyl-cis-decahydroisoquinoline
• CAS No.: 50640-76-1
• Molecular Formula: C₁₆H₂₃NO
• Molecular Weight: 245.365
• Mol file: 50640-76-1.mol

Synonyms:6-hydroxy-2-methyl-4a-phenyl-cis-decahydroisoquinoline

Chemical Property of 6-hydroxy-2-methyl-4a-phenyl-cis-decahydroisoquinoline

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 6-hydroxy-2-methyl-4a-phenyl-cis-decahydroisoquinoline

There total 21 articles about 6-hydroxy-2-methyl-4a-phenyl-cis-decahydroisoquinoline 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: 85.0%

(4aS,6S,8aS)-6-Formyloxy-4a-phenyl-octahydro-isoquinoline-2-carboxylic acid methyl ester (97523-15-4) → 6-hydroxy-2-methyl-4a-phenyl-cis-decahydroisoquinoline (50640-76-1)

Guidance literature:

With lithium aluminium tetrahydride; In tetrahydrofuran; for 6h; Ambient temperature;

DOI:10.1021/jo00219a006

Reference yield: 85.0%

(4aS,6S,8aS)-6-Formyloxy-4a-phenyl-octahydro-isoquinoline-2-carboxylic acid ethyl ester (97523-16-5) → 6-hydroxy-2-methyl-4a-phenyl-cis-decahydroisoquinoline (50640-76-1)

Guidance literature:

With lithium aluminium tetrahydride; In tetrahydrofuran; for 6h; Ambient temperature;

DOI:10.1021/jo00219a006

Reference yield:

ethyl 3-oxohept-6-enoate (17605-06-0) → 6-hydroxy-2-methyl-4a-phenyl-cis-decahydroisoquinoline (50640-76-1)

Guidance literature:

Multi-step reaction with 9 steps

1: NaBH₄ / propan-2-ol / 0.5 h / 0 °C

2: pyridine / 2 h / 80 °C

3: 72 percent / 1,7-diazabicyclo<5.4.0>undec-7-ene (DBU) / benzene / 2 h / Heating

4: 94 percent / CuI / diethyl ether / 1.5 h / 0 °C

5: 75 percent / NaOH / ethanol / 2 h / Heating

6: Et₃N, ClCOOMe, NaN₃ / acetone / 1.5 h / Ambient temperature

7: toluene / 3 h / Heating

8: 75 percent / 1.5 h / Ambient temperature

9: 85 percent / LiAlH₄ / tetrahydrofuran / 6 h / Ambient temperature

With pyridine; sodium hydroxide; sodium tetrahydroborate; copper(l) iodide; lithium aluminium tetrahydride; sodium azide; triethylamine; methyl chloroformate; 1,5-Diazabicyclo[5.4.0]undec-5-ene; In tetrahydrofuran; diethyl ether; ethanol; isopropyl alcohol; acetone; toluene; benzene;

DOI:10.1021/jo00219a006

upstream raw materials:

(4aS,6R,8aR)-6-Formyloxy-4a-phenyl-octahydro-isoquinoline-2-carboxylic acid methyl ester

ethyl (E)-3-phenylbut-2-enoate

2-(1-phenylethenyl)-5-hexen-1-ol

ethyl 2-(1-phenylethenyl)-5-hexenoate