[(3R,7R)-7-hydroxy-8-methyl-8-azabicyclo[3.2.1]oct-3-yl] 3-methylbutan oate

Base Information

• Chemical Name: [(3R,7R)-7-hydroxy-8-methyl-8-azabicyclo[3.2.1]oct-3-yl] 3-methylbutan oate
• CAS No.: 490-96-0
• Molecular Formula: C₁₃H₂₃NO₃
• Molecular Weight: 241.331
• Mol file: 490-96-0.mol

Synonyms:1aH,5aH-Tropane-3a,6b-diol, 3-isovalerate (8CI); Butanoic acid, 3-methyl-,6-hydroxy-8-methyl-8-azabicyclo[3.2.1]oct-3-yl ester, [1S-(3-endo,6-exo)]-;Valeroidine (6CI,7CI)

Chemical Property of [(3R,7R)-7-hydroxy-8-methyl-8-azabicyclo[3.2.1]oct-3-yl] 3-methylbutan oate

Chemical Property:

• Vapor Pressure: 1.73E-05mmHg at 25°C
• Boiling Point: 325.8°Cat760mmHg
• Flash Point: 150.8°C
• PSA: 49.77000
• Density: 1.11g/cm³
• LogP: 1.10960

Purity/Quality:

99%min ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Description: An alkaloid found in Duboisia myoporoides, the base crystallizes from EtOH in colourless, nacreous plates and has [α]20D - 9.0° (c 5.0, EtOH), or - 4.0° (c 5.0, H2O). It yields a crystalline hydrobromide as colourless needles, m.p. l70-2°C; [α]20D + 5.0° (c 20.0, H20); picrate, m.p. lS2-3°C; methiodide, m.p. 20S.SoC and the acetyl derivative, characterized as the hydrobromide, m.p. 197°C. The isovaleryl ester forms a hydrochloride, m.p. l24-SoC; [α]D + 2.6° (c 3.78, EtOH) and a hydrobromide, m.p. l76-7°C. Treatment of the hydrobromide with thionyl chloride gives norvaleroidine due to demethylation, a colourless syrup which furnishes a crystalline hydrobromide, m.p. 270°C; [α]20D + 1 ° (c 20.0, H20). On hydrolysis with aqueous Ba(OHh, the base gives dihydroxytropane and isovaleric acid while oxidation with KMn04 furnishes norvalieroidine and a base C13H190 4N, m.p. 136°C; [α]20D - 16.6° (c 7.4, EtOH).

Technology Process of [(3R,7R)-7-hydroxy-8-methyl-8-azabicyclo[3.2.1]oct-3-yl] 3-methylbutan oate

There total 19 articles about [(3R,7R)-7-hydroxy-8-methyl-8-azabicyclo[3.2.1]oct-3-yl] 3-methylbutan oate 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: 61.0%

(1R,3R,5S,6R)-6-(tert-butyldimethylsilyloxy)-8-methyl-8-azabicyclo[3.2.1]octan-3-yl 3-methylbutanoate (1529813-83-9) → 6β-Hydroxy-3α-isopentanoyloxytropan (490-96-0)

Guidance literature:

With toluene-4-sulfonic acid; In acetone; at 50 ℃; for 24h;

DOI:10.1007/s11426-013-4998-2

Reference yield:

(2R/S,3R)-1-methyl-5-oxo-2-(2-oxopropyl)pyrrolidin-3-yl acetate → 6β-Hydroxy-3α-isopentanoyloxytropan (490-96-0)

Guidance literature:

Multi-step reaction with 8 steps

1.1: acetyl chloride / ethanol / 0 - 20 °C

2.1: 1H-imidazole / tetrahydrofuran / 48 h / 20 °C

3.1: triethylamine / dichloromethane / 0 - 20 °C

4.1: 2,6-di-tert-butyl-4-methylpyridine; trifluoromethylsulfonic anhydride / dichloromethane / 0.67 h / -78 °C

4.2: -78 - 20 °C

5.1: tri-n-butyl-tin hydride / toluene / 5 h / 85 °C

6.1: platinum(IV) oxide; hydrogen / ethanol / 30 h / 20 °C / 38002.6 Torr

7.1: triethylamine / dichloromethane

8.1: toluene-4-sulfonic acid / acetone / 24 h / 50 °C

With 1H-imidazole; platinum(IV) oxide; 2,6-di-tert-butyl-4-methylpyridine; trifluoromethylsulfonic anhydride; hydrogen; tri-n-butyl-tin hydride; toluene-4-sulfonic acid; triethylamine; acetyl chloride; In tetrahydrofuran; ethanol; dichloromethane; acetone; toluene;

DOI:10.1007/s11426-013-4998-2

Reference yield:

(4R,5S)-4-hydroxy-1-methyl-5-(2-oxopropyl)pyrrolidin-2-one (1529813-79-3) → 6β-Hydroxy-3α-isopentanoyloxytropan (490-96-0)

Guidance literature:

Multi-step reaction with 7 steps

1.1: 1H-imidazole / tetrahydrofuran / 48 h / 20 °C

2.1: triethylamine / dichloromethane / 0 - 20 °C

3.1: 2,6-di-tert-butyl-4-methylpyridine; trifluoromethylsulfonic anhydride / dichloromethane / 0.67 h / -78 °C

3.2: -78 - 20 °C

4.1: tri-n-butyl-tin hydride / toluene / 5 h / 85 °C

5.1: platinum(IV) oxide; hydrogen / ethanol / 30 h / 20 °C / 38002.6 Torr

6.1: triethylamine / dichloromethane

7.1: toluene-4-sulfonic acid / acetone / 24 h / 50 °C

With 1H-imidazole; platinum(IV) oxide; 2,6-di-tert-butyl-4-methylpyridine; trifluoromethylsulfonic anhydride; hydrogen; tri-n-butyl-tin hydride; toluene-4-sulfonic acid; triethylamine; In tetrahydrofuran; ethanol; dichloromethane; acetone; toluene;

DOI:10.1007/s11426-013-4998-2

upstream raw materials:

(1R)-3endo-isovaleryloxy-6exo-phenylcarbamoyloxy-tropane; hydrochloride

isopentanoyl chloride

(1R)-6exo-phenylcarbamoyloxy-tropane-3endo-ol

(+/-)-6exo-phenylcarbamoyloxy-tropane-3endo-ol

Refernces