(1S,4S)-4,5,5-trimethyl-{[(phenyl)methoxy]acetyl}-2-azabicyclo[2.2.1]heptan-3-one

Base Information

• Chemical Name: (1S,4S)-4,5,5-trimethyl-{[(phenyl)methoxy]acetyl}-2-azabicyclo[2.2.1]heptan-3-one
• CAS No.: 442913-24-8
• Molecular Formula: C₁₈H₂₃NO₃
• Molecular Weight: 301.386
• Mol file: 442913-24-8.mol

Synonyms:(1S,4S)-4,5,5-trimethyl-{[(phenyl)methoxy]acetyl}-2-azabicyclo[2.2.1]heptan-3-one

Chemical Property of (1S,4S)-4,5,5-trimethyl-{[(phenyl)methoxy]acetyl}-2-azabicyclo[2.2.1]heptan-3-one

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (1S,4S)-4,5,5-trimethyl-{[(phenyl)methoxy]acetyl}-2-azabicyclo[2.2.1]heptan-3-one

There total 1 articles about (1S,4S)-4,5,5-trimethyl-{[(phenyl)methoxy]acetyl}-2-azabicyclo[2.2.1]heptan-3-one 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: 89.0%

Benzyloxyacetyl chloride (19810-31-2) + (1R,4S)-2-aza-4,5,5-trimethylbicyclo[2.2.1]heptan-3-one (442913-23-7) → (1S,4S)-4,5,5-trimethyl-{[(phenyl)methoxy]acetyl}-2-azabicyclo[2.2.1]heptan-3-one (442913-24-8)

Guidance literature:

(1R,4S)-2-aza-4,5,5-trimethylbicyclo[2.2.1]heptan-3-one; With n-butyllithium; In tetrahydrofuran; hexane; at 0 ℃; for 0.75h;

Benzyloxyacetyl chloride; In tetrahydrofuran; hexane; at -20 ℃; for 14h;

DOI:10.1002/hlca.200290026

Reference yield: 85.0%

(E)-4-methylpent-2-enal (24502-08-7) + (1S,4S)-4,5,5-trimethyl-{[(phenyl)methoxy]acetyl}-2-azabicyclo[2.2.1]heptan-3-one (442913-24-8) → (1S,4S)-3-[(4E)-3-hydroxy-6-methyl-2-phenylmetoxyhept-4-enoyl]-3-aza-1,6,6-trimethylbicyclo[2.2.1]heptan-2-one

Guidance literature:

With N-ethyl-N,N-diisopropylamine; diethylboron trifluoromethanesulfonate; In dichloromethane; at -50 ℃; for 9h;

DOI:10.1021/ol026101e

Reference yield: 85.0%

(E)-4-methylpent-2-enal (24502-08-7) + (1S,4S)-4,5,5-trimethyl-{[(phenyl)methoxy]acetyl}-2-azabicyclo[2.2.1]heptan-3-one (442913-24-8) → (1S,4S)-2-{(2S,3R,4E)-3-hydroxy-6-methyl-2-[(phenyl)methoxy]hept-4-enoyl}-4,5,5-trimethyl-2-azabicyclo[2.2.1]heptan-3-one (442913-25-9)

Guidance literature:

(1S,4S)-4,5,5-trimethyl-{[(phenyl)methoxy]acetyl}-2-azabicyclo[2.2.1]heptan-3-one; With N-ethyl-N,N-diisopropylamine; diethylboron trifluoromethanesulfonate; In dichloromethane; at -78 ℃; for 1h;

(E)-4-methylpent-2-enal; In dichloromethane; at -50 ℃; for 9h;

DOI:10.1002/hlca.200290026

upstream raw materials:

Benzyloxyacetyl chloride

(1R,4S)-2-aza-4,5,5-trimethylbicyclo[2.2.1]heptan-3-one

Downstream raw materials:

(1S,4S)-2-{(2S,3R,4E)-3-hydroxy-6-methyl-2-[(phenyl)methoxy]hept-4-enoyl}-4,5,5-trimethyl-2-azabicyclo[2.2.1]heptan-3-one

(2S,3R,4E)-3-{[(tert-butyl)dimethylsilyl]oxy}-6-methyl-2-[(phenyl)methoxy]hept-4-enal

S-ethyl (2S,3R,4E)-3-{[(tert-butyl)dimethylsilyl]oxy}-6-methyl-2-[(phenyl)methoxy]hept-4-enethioate

S-phenyl (2R,3R,4R,5R,6E)-5-{[(tert-butyl)dimethylsilyl]oxy}-3-hydroxy-2-methoxy-8-methyl-4-[(phenyl)methoxy]non-6-enethioate