Water → HCID 86650664, compound

HRID 1969466Notes

Reaction equation

HRID 1969466 reaction equation
C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].[CH3:15][C:16]([NH:28][C:29]1[C:30](=[O:51])[N:31]([C:40]2[CH:45]=[CH:44][C:43]([O:46][C:47]([F:50])([F:49])[F:48])=[CH:42][CH:41]=2)[C@@H:32]([C:34]2[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=2)[CH:33]=1)([C:18]1[CH:23]=[CH:22][CH:21]=[C:20]([C:24]([F:27])([F:26])[F:25])[N:19]=1)[CH3:17].FC(F)(F)C(O)=O.O>C1(C)C=CC=CC=1>[CH3:17][C:16]([NH:28][C@@H:29]1[CH2:33][C@H:32]([C:34]2[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=2)[N:31]([C:40]2[CH:41]=[CH:42][C:43]([O:46][C:47]([F:48])([F:50])[F:49])=[CH:44][CH:45]=2)[C:30]1=[O:51])([C:18]1[CH:23]=[CH:22][CH:21]=[C:20]([C:24]([F:27])([F:26])[F:25])[N:19]=1)[CH3:15]

Participants

6

Reactant 4

HCID 962WaterHCID 6422Trifluoroacetic acidHCID 5049666Sodium triacetoxyborohydrideHCID 86650663HCID 86650663, compound

Product 1

HCID 86650664HCID 86650664, compoundYield 99%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

Add sodium triacetoxyborohydride (98 g, 465 mmol) in two portions to a solution of (R)-3-[1-methyl-1-(6-trifluoromethyl-pyridin-2-yl)-ethylamino]-1-(4-trifluoromethoxy-phenyl)-5-phenyl-1,5-dihydro-pyrrol-2-one (173 g, 332 mmol) and trifluoroacetic acid (50 mL, 664 mmol) in toluene (1.7 L). Stir for 3 hours and cannulate the mixture into water (2.5 L) over a period of 20 minutes. Extract the water with MTBE (2 L) and wash with water and sodium bicarbonate and concentrate to obtain the title compound as a tan oil (172 g, 98%). 1H NMR (400 MHz, DMSO-d6) δ 8.07 (m, 2H), 7.71 (d, J=8 Hz, 1H), 7.39 (d, J=12 Hz, 2H), 7.21 (m, 8H), 5.16 (m, 1H), 3.42 (m, 1H), 2.68 (m, 1H), 1.63 (m, 1H), 1.38 (s, 3H), 1.43 (s, 3H).

Workup

  1. extractionExtract the water with MTBE (2 L)
  2. washwash with water and sodium bicarbonate
  3. concentrationconcentrate

Sources & evidence

ORD record
ord-32bc7d0916bc4a35bc5ac3aaf39a35ad
Source dataset
uspto-grants-2013_04
Patent number
US08426448B2

Reaction notes

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