DL-EXO-6-HYDROXYTROPINONE)

Base Information

• Chemical Name: DL-EXO-6-HYDROXYTROPINONE)
• CAS No.: 60873-19-0
• Molecular Formula: C8H13NO2
• Molecular Weight: 155.197
• Hs Code.: 2933990090
• Mol file: 60873-19-0.mol

Synonyms:DL-EXO-6-HYDROXYTROPINONE)

Chemical Property of DL-EXO-6-HYDROXYTROPINONE)

Chemical Property:

• PSA: 40.54000
• LogP: -0.27920

Purity/Quality:

99%min ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of DL-EXO-6-HYDROXYTROPINONE)

There total 1 articles about DL-EXO-6-HYDROXYTROPINONE) 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:

2,5-dihydro-2,5-dimethoxyfuran (332-77-4) + acetonedicarboxylic acid (542-05-2) + methylamine hydrochloride (593-51-1) → 6β-hydroxy-8-methyl-8-azabicyclo<3.2.1>octan-3-one (5932-53-6,54382-90-0,60873-19-0,110061-26-2,133867-56-8,143393-92-4)

Guidance literature:

With hydrogenchloride; sodium acetate; potassium carbonate; In water; for 48h; Ambient temperature; pH=4-5;

Reference yield:

(1R,5R,6S)-6-Hydroxy-8-methyl-8-aza-bicyclo[3.2.1]octan-3-one (60873-19-0) → (1R,3S,5S)-8-methyl-8-azabicyclo[3.2.1]oct-6-en-3-ol (20513-09-1)

Guidance literature:

Multi-step reaction with 5 steps

1: toluene-4-sulfonic acid / benzene / 3 h / Reflux; Dean-Stark

2: triethylamine; dmap / dichloromethane / 20 °C

3: potassium tert-butylate / tetrahydrofuran / 20 °C

4: hydrogenchloride / tetrahydrofuran; water / 16 h / 20 °C

5: L-Selectride / tetrahydrofuran / 1 h / -78 - 20 °C

With hydrogenchloride; dmap; potassium tert-butylate; L-Selectride; toluene-4-sulfonic acid; triethylamine; In tetrahydrofuran; dichloromethane; water; benzene;

DOI:10.1002/ejoc.201501430

Reference yield:

(1R,5R,6S)-6-Hydroxy-8-methyl-8-aza-bicyclo[3.2.1]octan-3-one (60873-19-0) → ((endo)-8-methyl-8-azabicyclo[3.2.1]oct-3-yl)methanol (142892-37-3)

Guidance literature:

Multi-step reaction with 9 steps

1: 97 percent / pyridine

2: 1) t-BuOK / 1) THF, 0 deg C, 20 min, 2) THF, 25 deg C, 50 min

3: 89 percent / 0.18 N NaOH / 12 h / 25 °C

4: 1) triphenylmethane, n-BuLi / 1) THF, 0 deg C, 10 min, 2) THF, 0 deg C, 2.5 h

5: 1) disiamylborane, 2) 30percent aq. H₂O₂, 3 N NaOH / 1) THF, 0 deg C, 30 min, 2) methanol, 0 deg C

6: 99 percent / TsOH*H₂O / 2.5 h / 0 °C

7: potassium t-BuOK / dimethylsulfoxide / 25 °C

8: 0.1 N aq. HCl / methanol / 0.75 h

9: 1.7 mg / H₂ / 10 percent Pd on charcoal / methanol / 2.5 h / 1344.6 - 2223.7 Torr / Ambient temperature

With pyridine; hydrogenchloride; sodium hydroxide; n-butyllithium; triphenylmethane; potassium tert-butylate; hydrogen; dihydrogen peroxide; bis-(1,2-dimethylpropyl)borane; toluene-4-sulfonic acid; palladium on activated charcoal; In methanol; dimethyl sulfoxide;

DOI:10.1016/S0040-4020(01)81578-7

upstream raw materials:

2,5-dihydro-2,5-dimethoxyfuran

acetonedicarboxylic acid

methylamine hydrochloride

Downstream raw materials:

phenyl-carbamic acid-(3-oxo-tropane-6exo-yl ester)

(+/-)-8-methyl-8-azabicyclo[3.2.1]octan-β-ol

(+/-)-8-methyl-8-azabicyclo[3.2.1]octan-α-ol

Refernces