Hydrochloric Acid → (3R,4R)-1-tert-butyl-3-({3-cyclohexyl-3-[(methylsulfonyl)methyl]-8-azabicyclo[3.2.1]oct-8-yl}carbonyl)-4-(2,4-difluorophenyl)pyrrolidinium chloride

HRID 1178901Notes

Reaction equation

HRID 1178901 reaction equation
[Cl-:1].[C:2]([NH+:6]1[CH2:10][C@@H:9]([C:11]2[CH:16]=[CH:15][C:14]([F:17])=[CH:13][C:12]=2[F:18])[C@@H:8]([C:19]([N:21]2[CH:26]3[CH2:27][CH2:28][CH:22]2[CH2:23][C:24]([CH:33]2[CH2:38][CH2:37][CH2:36][CH2:35][CH2:34]2)([CH2:29][S:30]([CH3:32])=[O:31])[CH2:25]3)=[O:20])[CH2:7]1)([CH3:5])([CH3:4])[CH3:3].[OH:39]OS([O-])=O.[K+].Cl>C(O)C.O.CCOCC>[Cl-:1].[C:2]([NH+:6]1[CH2:10][C@@H:9]([C:11]2[CH:16]=[CH:15][C:14]([F:17])=[CH:13][C:12]=2[F:18])[C@@H:8]([C:19]([N:21]2[CH:26]3[CH2:27][CH2:28][CH:22]2[CH2:23][C:24]([CH:33]2[CH2:34][CH2:35][CH2:36][CH2:37][CH2:38]2)([CH2:29][S:30]([CH3:32])(=[O:39])=[O:31])[CH2:25]3)=[O:20])[CH2:7]1)([CH3:5])([CH3:3])[CH3:4]

Participants

7

Reactant 3

HCID 313Hydrochloric AcidHCID 23707502Potassium hydroxy sulfiteHCID 86607402(3R,4R)-1-tert-butyl-3-({3-cyclohexyl-3-[(methylsulfinyl)methyl]-8-azabicyclo[3.2.1]oct-8-yl}carbonyl)-4-(2,4-difluorophenyl)pyrrolidinium chloride

Product 1

HCID 86607404(3R,4R)-1-tert-butyl-3-({3-cyclohexyl-3-[(methylsulfonyl)methyl]-8-azabicyclo[3.2.1]oct-8-yl}carbonyl)-4-(2,4-difluorophenyl)pyrrolidinium chloride

Reagents, catalysts & solvents 3

HCID 702EthanolSolventHCID 962WaterSolventHCID 3283Diethyl EtherSolvent

Procedure

To a solution of (3R,4R)-1-tert-butyl-3-({3-cyclohexyl-3-[(methylsulfinyl)methyl]-8-azabicyclo[3.2.1]oct-8-yl}carbonyl)-4-(2,4-difluorophenyl)pyrrolidinium chloride (3-8) (50 mg, 0.090 mmol) in ethanol (2.0 mL) was added a solution of the oxone® (276 mg, 0.451 mmol) in 2.0 mL of water. The mixture was stirred at room temperature for 40 min. The solid was filtered and filtrate was concentrated, diluted with methylene chloride dried over anhydrous Na2SO4, filtered, and concentrated, followed by the addition of one equivalent HCl in ether to afford (3-9) as white solid (in/z (ES) 551 (MH+)).

Workup

  1. filtrationThe solid was filtered
  2. concentrationfiltrate was concentrated
  3. additiondiluted with methylene chloride
  4. dry with materialdried over anhydrous Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-434dcdec71444a8fbb6e9221e76f9bb8
Source dataset
uspto-grants-2007_10
Patent number
US07276520B2

Reaction notes

Loading…