تفاعل #1702103

معادلة التفاعل

ethyl acetate dichloromethane

(1S,6S)-4,6-Dimethyl-cyclohex-3-ene-carboxylic acid [5-(3,3-dimethyl-but-1-ynyl)-thiophen-3-yl]-(trans-4-hydroxy-cyclohexyl)-amide

lithium diisopropylamine

→

title compound

5-(3,3-Dimethyl-but-1-ynyl)-3-[(1S,6S)-(4,6-dimethyl-cyclohex-3-enecarbonyl)-(4-hydroxy-cyclohexyl)-amino]-thiophene-2-carboxylic acid

المذيبات

THF

ظروف التفاعل

المعالجة

1. 1
   أخرىCO2 was vigorously bubbled through the reaction solution for 10 minutes
2. 2
   أخرىThe reaction was then quenched with the addition of iPrOH
3. 3
   workup.ADDITIONdiluted with ethyl acetate
4. 4
   غسيلwashed with saturated NH4Cl(aq)
5. 5
   تجفيفdried over MgSO4
6. 6
   ترشيحfiltered
7. 7
   تركيزconcentrated

الإجراء التجريبي

(1S,6S)-4,6-Dimethyl-cyclohex-3-ene-carboxylic acid [5-(3,3-dimethyl-but-1-ynyl)-thiophen-3-yl]-(trans-4-hydroxy-cyclohexyl)-amide (1.74 g, 4.2 mmol) in THF (50 mL) was cooled to −78° C. and treated with lithium diisopropylamine (8.4 mL, 2.0M in heptane/THF/PhEt, 16.8 mmol) and allowed to warm to 0° C. over the course of 2 hours. CO2 was vigorously bubbled through the reaction solution for 10 minutes. The reaction was then quenched with the addition of iPrOH, diluted with ethyl acetate, washed with saturated NH4Cl(aq), dried over MgSO4, filtered, and concentrated. Silica gel chromatography (0-100% ethyl acetate/dichloromethane) afforded 530 mg (1.2 mmol) of the title compound: MS (m/z): 458.1 [M+H]+; HPLC retention time 4.35 min (2-98% acetonitrile: water with 0.05% trifluoroacetic acid).

المصدر