(1R,2R,6S,7R,9R)-4,4-Dimethyl-8-[(S)-2-phenylethyl]-3,5-dioxa-8-azatricyclo[5.2.1.0^2,6]decane-9-carbaldehyde

Base Information

• Chemical Name: (1R,2R,6S,7R,9R)-4,4-Dimethyl-8-[(S)-2-phenylethyl]-3,5-dioxa-8-azatricyclo[5.2.1.0^2,6]decane-9-carbaldehyde
• CAS No.: 347381-75-3
• Molecular Formula: C₁₈H₂₃NO₃
• Molecular Weight: 301.386

Synonyms:(1R,2R,6S,7R,9R)-4,4-Dimethyl-8-[(S)-2-phenylethyl]-3,5-dioxa-8-azatricyclo[5.2.1.0^2,6]decane-9-carbaldehyde

Chemical Property of (1R,2R,6S,7R,9R)-4,4-Dimethyl-8-[(S)-2-phenylethyl]-3,5-dioxa-8-azatricyclo[5.2.1.0^2,6]decane-9-carbaldehyde

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (1R,2R,6S,7R,9R)-4,4-Dimethyl-8-[(S)-2-phenylethyl]-3,5-dioxa-8-azatricyclo[5.2.1.0^2,6]decane-9-carbaldehyde

There total 4 articles about (1R,2R,6S,7R,9R)-4,4-Dimethyl-8-[(S)-2-phenylethyl]-3,5-dioxa-8-azatricyclo[5.2.1.0^2,6]decane-9-carbaldehyde 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:

[(1R,2R,6S,7R,9R)-4,4-Dimethyl-8-((S)-1-phenyl-ethyl)-3,5-dioxa-8-aza-tricyclo[5.2.1.02,6]dec-9-yl]-methanol (347381-84-4) → (1R,2R,6S,7R,9R)-4,4-Dimethyl-8-[(S)-2-phenylethyl]-3,5-dioxa-8-azatricyclo[5.2.1.02,6]decane-9-carbaldehyde (347381-75-3)

Guidance literature:

With oxalyl dichloride; TEA; dimethyl sulfoxide; In dichloromethane; at -78 ℃;

DOI:10.1002/1521-3765(20010401)7:7<1431::AID-CHEM1431>3.0.CO;2-L

Reference yield:

(1R,3R,4S)-2-[(1S)-1-phenylethyl]-2-azabicyclo[2.2.1]hept-5-ene-3-carboxylic acid methyl ester (130195-74-3) → (1R,2R,6S,7R,9R)-4,4-Dimethyl-8-[(S)-2-phenylethyl]-3,5-dioxa-8-azatricyclo[5.2.1.02,6]decane-9-carbaldehyde (347381-75-3)

Guidance literature:

Multi-step reaction with 4 steps

1: 100 percent / aq. NMO; OsO₄ / 2-methyl-propan-2-ol / 12 h / 20 °C

2: 89 percent / p-TsOH / methanol / 12 h / 40 - 50 °C

3: LiAlH₄ / tetrahydrofuran / 1 h / 0 °C

4: DMSO; oxalyl chloride; TEA / CH₂Cl₂ / -78 °C

With osmium(VIII) oxide; lithium aluminium tetrahydride; N-methyl-2-indolinone; oxalyl dichloride; TEA; toluene-4-sulfonic acid; dimethyl sulfoxide; In tetrahydrofuran; methanol; dichloromethane; tert-butyl alcohol; 4: Swern oxidation;

DOI:10.1002/1521-3765(20010401)7:7<1431::AID-CHEM1431>3.0.CO;2-L

Reference yield:

(1R,2R,6S,7R,9R)-4,4-Dimethyl-8-[(S)-1-phenylethyl]-3,5-dioxa-8-azatricyclo[5.2.1.02,6]decane-9-carboxylic acid methyl ester (347381-71-9) → (1R,2R,6S,7R,9R)-4,4-Dimethyl-8-[(S)-2-phenylethyl]-3,5-dioxa-8-azatricyclo[5.2.1.02,6]decane-9-carbaldehyde (347381-75-3)

Guidance literature:

Multi-step reaction with 2 steps

1: LiAlH₄ / tetrahydrofuran / 1 h / 0 °C

2: DMSO; oxalyl chloride; TEA / CH₂Cl₂ / -78 °C

With lithium aluminium tetrahydride; oxalyl dichloride; TEA; dimethyl sulfoxide; In tetrahydrofuran; dichloromethane; 2: Swern oxidation;

DOI:10.1002/1521-3765(20010401)7:7<1431::AID-CHEM1431>3.0.CO;2-L

upstream raw materials:

[(1R,2R,6S,7R,9R)-4,4-Dimethyl-8-((S)-1-phenyl-ethyl)-3,5-dioxa-8-aza-tricyclo[5.2.1.0^2,6]dec-9-yl]-methanol

(1R,3R,4S)-2-[(1S)-1-phenylethyl]-2-azabicyclo[2.2.1]hept-5-ene-3-carboxylic acid methyl ester

(1R,3R,4R,5R,6S)-methyl 5,6-dihydroxy-2-((S)-1-phenylethyl)-2-azabicyclo[2.2.1]heptane-3-carboxylate

(1R,2R,6S,7R,9R)-4,4-Dimethyl-8-[(S)-1-phenylethyl]-3,5-dioxa-8-azatricyclo[5.2.1.0^2,6]decane-9-carboxylic acid methyl ester

Downstream raw materials:

(R)-1-[(1R,2R,6S,7R,9R)-4,4-Dimethyl-8-((S)-1-phenyl-ethyl)-3,5-dioxa-8-aza-tricyclo[5.2.1.0^2,6]dec-9-yl]-ethanol

1-[(1R,2R,6S,7R,9R)-4,4-Dimethyl-8-[(S)-1-phenylethyl]-3,5-dioxa-8-aza-tricyclo[5.2.0^2,6]dec-9-yl]ethanone

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