Dichloromethane → HCID 87160620, compound

HRID 2206922Notes

Reaction equation

HRID 2206922 reaction equation
[F:1][C:2]([F:38])([F:37])[C:3]1[CH:4]=[C:5]([C:13]2([C:33]([F:36])([F:35])[F:34])[CH2:17][CH2:16][N:15]([C:18]3[CH:28]=[CH:27][C:21]([C:22](OCC)=[O:23])=[C:20]([C:29]([F:32])([F:31])[F:30])[N:19]=3)[CH2:14]2)[CH:6]=[C:7]([C:9]([F:12])([F:11])[F:10])[CH:8]=1.ClCCl.[H-].C([Al+]CC(C)C)C(C)C.O.O.O.O.O.O.O.O.O.O.S([O-])([O-])(=O)=O.[Na+].[Na+]>C(OCC)(=O)C.CCCCCC>[F:12][C:9]([F:10])([F:11])[C:7]1[CH:6]=[C:5]([C:13]2([C:33]([F:34])([F:35])[F:36])[CH2:17][CH2:16][N:15]([C:18]3[N:19]=[C:20]([C:29]([F:30])([F:31])[F:32])[C:21]([CH2:22][OH:23])=[CH:27][CH:28]=3)[CH2:14]2)[CH:4]=[C:3]([C:2]([F:38])([F:37])[F:1])[CH:8]=1

Participants

7

Reactant 4

HCID 6344DichloromethaneHCID 62649Sodium sulfate decahydrateHCID 21225700DiisobutylaluminumhydrideHCID 87160624Ethyl 6-{3-[3,5-bis(trifluoromethyl)phenyl]-3-(trifluoromethyl)pyrrolidin-1-yl}-2-(trifluoro-methyl)nicotinate

Product 1

HCID 87160620HCID 87160620, compoundYield 98.5%

Reagents, catalysts & solvents 2

HCID 8058HexaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

Ethyl 6-{3-[3,5-bis(trifluoromethyl)phenyl]-3-(trifluoromethyl)pyrrolidin-1-yl}-2-(trifluoro-methyl)nicotinate (1.7 g) was added to dichloromethane (50 ml). Then, 1.0 mol/l hexane solution (10 ml) of diisobutyl aluminum hydride was added dropwise thereto at −70° C. After continuing the stirring at −70° C. for 30 minutes, ethyl acetate (50 ml) and sodium sulfate decahydrate (3.0 g) were added. After further stirring at room temperature for 1 hour, the reaction liquid was filtered by suction on Celite. The filtrate was distilled off under reduced pressure and the purified by silica gel column chromatography to obtain [6-{3-[3,5-bis-(trifluoromethyl)phenyl]-3-(trifluoromethyl)pyrrolidin-1-yl}-2-(trifluoromethyl)pyridin-3-yl]-methanol (1.55 g).

Workup

  1. customat −70° C
  2. customstirring at −70° C.
  3. customfor 30 minutes
  4. customthe reaction liquid
  5. filtrationwas filtered by suction on Celite
  6. distillationThe filtrate was distilled off under reduced pressure
  7. customthe purified by silica gel column chromatography

Sources & evidence

ORD record
ord-a9b4d39a6ad24c0caffe15482bafe080
Source dataset
uspto-grants-2016_06
Patent number
US09375000B2

Reaction notes

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