ChemicalBook CAS DataBase List 2-Thiopheneacetic acid, α-hydroxy-α-2-thienyl-, (3R)-1-azabicyclo[2.2.2]oct-3-yl ester

2-Thiopheneacetic acid, α-hydroxy-α-2-thienyl-, (3R)-1-azabicyclo[2.2.2]oct-3-yl ester synthesis

8synthesis methods

Product Name:2-Thiopheneacetic acid, α-hydroxy-α-2-thienyl-, (3R)-1-azabicyclo[2.2.2]oct-3-yl ester
CAS Number:320347-97-5
Molecular formula:C17H19NO3S2
Molecular Weight:349.46

2-HYDROXY-2,2-BIS(2-THIENYL) ACETIC ACID

4746-63-8
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25333-42-0 Synthesis

25333-42-0
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2-Thiopheneacetic acid, α-hydroxy-α-2-thienyl-, (3R)-1-azabicyclo[2.2.2]oct-3-yl ester

320347-97-5
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Yield:320347-97-5 89.05%

Reaction Conditions:

Stage #1: (R)-quinuclidin-3-olwith sodium methylate in cyclohexane at 80 - 85;Large scale;
Stage #2: 2-hydroxy-2,2-di(thiophen-2-yl)acetic acid in cyclohexane at 80 - 85;Large scale;

Steps:

2 Example-2: Preparation of l-azabicyclo[2.2.2]oct-3-ylhydroxy(dithiophen-2- yl)acetate

Example-2: Preparation of l-azabicyclo[2.2.2]oct-3-ylhydroxy(dithiophen-2- yl)acetate To the 10 lit Cyclohexane added 0.638 kg (3R)-l-azabicyclo[2.2.2]octan-3-ol and 0.266 kg Sodium Methoxide Powder and heated upto 80-85° C. Simultaneously distilled out slowly 5.0 lit Cyclohexane and added 5.0 lit Cyclohexane and again distilled out by azeotrophically slowly 8.0 lit. Added 8.01it L Fresh Cyclohexane and stirred for 3-4 hr at 80-85° C. Added 1.0 kg of methyl hydroxy (dithiophen-2-yl) acetate lot wise over a period of 20-30 min. Stirred and maintained for 3-4 hrs at 80-85° C. Cyclohexane Distilled out and degased completely under vacuum at below 85° C. Added 10. L DM- Water at 25-30° C and stirred for lhr. Filtered and washed with 2.0 L DM water and slurry washed with 4.01it Cyclohexane two time. Filtered the product, suck dried and washed with 1.0 L Cyclohexane and suck dried for 10-15 min to get 89.05% titled product. HPLC purity: 97.68%

References:

WO2016/162878,2016,A1 Location in patent:Page/Page column 16

26447-85-8 Synthesis