2,6-Lutidine → HCID 86650317, compound

HRID 2368636Notes

Reaction equation

HRID 2368636 reaction equation
[CH:1]1([C:6]2[C:15]3[C@@H:14]([OH:16])[CH2:13][C:12]([CH3:18])([CH3:17])[CH2:11][C:10]=3[N:9]=[C:8]([CH:19]([O:21][CH3:22])[CH3:20])[C:7]=2[C:23]2[C:24]([C:31]([F:34])([F:33])[F:32])=[CH:25][CH:26]=[C:27]([CH:29]=[O:30])[CH:28]=2)[CH2:5][CH2:4][CH2:3][CH2:2]1.N1C(C)=CC=CC=1C.[C:43]([Si:47](OS(C(F)(F)F)(=O)=O)([CH3:49])[CH3:48])([CH3:46])([CH3:45])[CH3:44]>C1(C)C=CC=CC=1>[C:43]([Si:47]([CH3:49])([CH3:48])[O:16][C@H:14]1[CH2:13][C:12]([CH3:17])([CH3:18])[CH2:11][C:10]2[N:9]=[C:8]([CH:19]([O:21][CH3:22])[CH3:20])[C:7]([C:23]3[C:24]([C:31]([F:34])([F:32])[F:33])=[CH:25][CH:26]=[C:27]([CH:29]=[O:30])[CH:28]=3)=[C:6]([CH:1]3[CH2:2][CH2:3][CH2:4][CH2:5]3)[C:15]1=2)([CH3:46])([CH3:45])[CH3:44]

Participants

5

Reactant 3

HCID 79372,6-LutidineHCID 123564tert-Butyldimethylsilyl trifluoromethanesulphonateHCID 86650318HCID 86650318, compound

Product 1

HCID 86650317HCID 86650317, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
-18 °C

Procedure

840 mg 5-(S)-[4-Cyclopentyl-5-hydroxy-2-(1-methoxy-ethyl)-7,7-dimethyl-5,6,7,8-tetrahydro-quinolin-3-yl]-(4-trifluoromethyl-phenyl)-methanone (Diastereomer 1) are dissolved in 20 ml toluene, 823 μl 2,6-lutidine are added and the solution is cooled to −18° C. 811 μl Trifluoromethanesulfonic acid-tert.-butyldimethylsilylester are added dropwise and the mixture is stirred for further 20 minutes at −18° C. Then it is warmed to 0° C. and stirred for 1 hour whereafter the mixture is partitioned between saturated aqueous ammonium chloride solution and ethylacetate. The aqueous phase is twice extracted with ethylacetate and the combined organic phases are washed with brine. After drying with magnesium sulphate the solvents are evaporated in vacuo and the residue is chromatographed on silica gel (cyclohexane/ethylacetate 95:5 to 80:20).

Workup

  1. temperatureThen it is warmed to 0° C.
  2. stirringstirred for 1 hour whereafter the mixture
  3. customis partitioned between saturated aqueous ammonium chloride solution and ethylacetate
  4. extractionThe aqueous phase is twice extracted with ethylacetate
  5. washthe combined organic phases are washed with brine
  6. dry with materialAfter drying with magnesium sulphate the solvents
  7. customare evaporated in vacuo
  8. customthe residue is chromatographed on silica gel (cyclohexane/ethylacetate 95:5 to 80:20)

Sources & evidence

ORD record
ord-1bb278edfcfc4697a1a17cf5914a2c66
Source dataset
uspto-grants-2014_04
Patent number
US08703793B2

Reaction notes

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