Potassium trimethylsilanolate → [2-(1-{[(3S,4R)-1-Tert-Butyl-4-(2,4-Difluorophenyl)Pyrrolidin-3-yl]Carbonyl}Piperidin-4-yl)-5-Chlorophenyl]Acetic Acid

HRID 2415544Notes

Reaction equation

HRID 2415544 reaction equation
C[Si](C)(C)[O-].[K+].[C:7]([N:11]1[CH2:15][C@@H:14]([C:16]2[CH:21]=[CH:20][C:19]([F:22])=[CH:18][C:17]=2[F:23])[C@H:13]([C:24]([N:26]2[CH2:31][CH2:30][CH:29]([C:32]3[CH:37]=[CH:36][C:35]([Cl:38])=[CH:34][C:33]=3[CH2:39][C:40]([O:42]C)=[O:41])[CH2:28][CH2:27]2)=[O:25])[CH2:12]1)([CH3:10])([CH3:9])[CH3:8]>O1CCCC1>[C:7]([N:11]1[CH2:15][C@@H:14]([C:16]2[CH:21]=[CH:20][C:19]([F:22])=[CH:18][C:17]=2[F:23])[C@H:13]([C:24]([N:26]2[CH2:27][CH2:28][CH:29]([C:32]3[CH:37]=[CH:36][C:35]([Cl:38])=[CH:34][C:33]=3[CH2:39][C:40]([OH:42])=[O:41])[CH2:30][CH2:31]2)=[O:25])[CH2:12]1)([CH3:10])([CH3:8])[CH3:9]

Participants

4

Reactant 2

HCID 23668039Potassium trimethylsilanolateHCID 86590372Methyl [2-(1-{[(3S,4R)-1-Tert-Butyl-4-(2,4-Difluorophenyl)Pyrrolidin-3-yl]Carbonyl}Piperidin-4-yl)-5-Chlorophenyl]acetate

Product 1

HCID 69717242[2-(1-{[(3S,4R)-1-Tert-Butyl-4-(2,4-Difluorophenyl)Pyrrolidin-3-yl]Carbonyl}Piperidin-4-yl)-5-Chlorophenyl]Acetic Acid

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Potassium trimethylsilanolate (0.900 g, 7.05 mmol) was added to a stirred solution of methyl [2-(1-{[(3S,4R)-1-tert-butyl-4-(2,4-difluorophenyl)pyrrolidin-3-yl]carbonyl}-piperidin-4-yl)-5-chlorophenyl]acetate (1-9) (1.25 g, 2.35 mmol) in tetrahydrofuran (24 mL) at room temperature. After approximately 15 h, the volatiles were evaporated in vacuo and the crude residue was treated with a saturated solution of hydrogen chloride in ethyl acetate. After approximately 5 min, the reaction mixture was concentrated under reduced pressure and the crude residue triturated twice with dry diethyl ether to give 1-10 as an amorphous white solid (m/z (ES) 519 (MH+).

Workup

  1. customthe volatiles were evaporated in vacuo
  2. additionthe crude residue was treated with a saturated solution of hydrogen chloride in ethyl acetate
  3. waitAfter approximately 5 min
  4. concentrationthe reaction mixture was concentrated under reduced pressure
  5. customthe crude residue triturated twice with dry diethyl ether

Sources & evidence

ORD record
ord-acb945ecf25b44b896e625b2cb4cb6a8
Source dataset
uspto-grants-2004_11
Patent number
US06818658B2

Reaction notes

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