490-96-0

Basic information

• Product Name: [(3R,7R)-7-hydroxy-8-methyl-8-azabicyclo[3.2.1]oct-3-yl] 3-methylbutan oate
• Synonyms: [(3R,7R)-7-hydroxy-8-methyl-8-azabicyclo[3.2.1]oct-3-yl] 3-methylbutan oate;Valeroidine
• CAS NO: 490-96-0
• Molecular Formula: C13H23NO3
• Molecular Weight: 241.33
• Mol File: 490-96-0.mol
• Article Data: 1

Chemical Properties

• Boiling Point: 325.8°Cat760mmHg
• Flash Point: 150.8°C
• Appearance: /
• Density: 1.11g/cm³
• Vapor Pressure: 1.73E-05mmHg at 25°C
• Refractive Index: 1.516
• CAS DataBase Reference: [(3R,7R)-7-hydroxy-8-methyl-8-azabicyclo[3.2.1]oct-3-yl] 3-methylbutan oate(CAS DataBase Reference)
• NIST Chemistry Reference: [(3R,7R)-7-hydroxy-8-methyl-8-azabicyclo[3.2.1]oct-3-yl] 3-methylbutan oate(490-96-0)
• EPA Substance Registry System: [(3R,7R)-7-hydroxy-8-methyl-8-azabicyclo[3.2.1]oct-3-yl] 3-methylbutan oate(490-96-0)

Safety Data

• Hazardous Substances Data: 490-96-0(Hazardous Substances Data)

Usage

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).

References

Barger, Martin, Mitchell.,!. Chem. Soc., 1820 (1937) Barger, Martin, Mitchell., ibid, 1685 (1938) Martin, Mitchell., ibid, 1155 (I 940) Mitchell, Troutner., ibid, 1330 (I 947) Fodor, Kovacs., ibid, 2341 (1953) Fodor, Vincze, Toth., ibid, 1349 (1957) Fodor, Vincze, Toth., ibid, 3219 (1961)

InChI:InChI=1/C13H23NO3/c1-8(2)4-13(16)17-10-5-9-6-12(15)11(7-10)14(9)3/h8-12,15H,4-7H2,1-3H3/t9?,10-,11?,12-/m1/s1

Upstream product

• 102290-00-6 (1R)-3endo-isovaleryloxy-6exo-phenylcarbamoyloxy-tropane; hydrochloride 
• 1529813-79-3 (4R,5S)-4-hydroxy-1-methyl-5-(2-oxopropyl)pyrrolidin-2-one 
• 1529813-80-6 (4R,5S)-4-(tert-butyldimethylsilyloxy)-1-methyl-5-(2-oxopropyl)pyrrolidin-2-one 
• 1529813-82-8 (1S,5S,6R)-6-(tert-butyldimethylsilyloxy)-8-methyl-8-azabicyclo[3.2.1]octan-3-one 
• 1529813-83-9 (1R,3R,5S,6R)-6-(tert-butyldimethylsilyloxy)-8-methyl-8-azabicyclo[3.2.1]octan-3-yl 3-methylbutanoate 
• 1448179-64-3 (4S,5R)-4-(tert-butyldimethylsilyloxy)-1-methyl-5-(2-oxopropan-1-yl)pyrrolidin-2-one 
• 1448179-65-4 C₂₀H₄₁NO₃Si₂ 
• 102290-00-6 (+/-)-3endo-isovaleryloxy-6exo-phenylcarbamoyloxy-tropane; hydrochloride 
• 97317-61-8 (+/-)-6exo-phenylcarbamoyloxy-tropane-3endo-ol 
• 97317-61-8 (1R)-6exo-phenylcarbamoyloxy-tropane-3endo-ol 
• 108-12-3 isopentanoyl chloride 

Relevant articles and documents

A novel and versatile method for the enantioselective syntheses of tropane alkaloids

A full account of the novel and flexible approach to hydroxylated 8-azabicyclo[3,2,1]octan-3-ones and 9-azabicyclo[3,3,1] nonan-3-ones is presented. Using keto-lactams as the starting materials, this two-step method consists of silyl enol ether formation with TBDMSOTf, lactam activation with Tf2O/DTBMP, and halide-promoted cyclization. Radical dechlorination of the resulting 1-halotropan-3-ones led to the corresponding hydroxylated tropan-3-ones, which can be hydrogenated to yield 3α,6β- dihydroxytropanes. Starting from optically active keto-lactams, the method has been applied to the enantioselective syntheses of (+)-(1S,3S,5R,6S)-pervilleine C (6), (+)-(1S,3R,5S,6R)-valeroidine (3), (+)-(1S,3S,5R,6S)-dibenzoyloxytropane (8), and (+)-(1S,3S,5R,6S)-merredissine (9).