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Hydrochloric Acid → (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

HRID 1178900
Notes
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Reaction equation

HRID 1178900 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:32]2[CH2:37][CH2:36][CH2:35][CH2:34][CH2:33]2)([CH2:29][S:30][CH3:31])[CH2:25]3)=[O:20])[CH2:7]1)([CH3:5])([CH3:4])[CH3:3].Cl.C([OH:41])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:32]2[CH2:33][CH2:34][CH2:35][CH2:36][CH2:37]2)([CH2:29][S:30]([CH3:31])=[O:41])[CH2:25]3)=[O:20])[CH2:7]1)([CH3:5])([CH3:3])[CH3:4]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 702EthanolHCID 86607400HCID 86607400, compound

Product 1

HCID 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

Reagents, catalysts & solvents 2

HCID 962WaterSolvent
HCID 3283Diethyl EtherSolvent

Procedure

To a solution of (3R,4R)-1-tert-butyl-3-({3-cyclohexyl-3-[(methylthio)methyl]-8-azabicyclo[3.2.1]oct-8-yl}carbonyl)-4-(2,4-difluorophenyl)pyrrolidinium chloride (3-7) (0.150 g, 0.0270 mmol) in ethanol (6.0 mL) was added a solution of NaIO4 (0.174 g, 0.813 mmol) in 6.0 mL of water. The mixture was stirred at room temperature for 50 min. The solid was filtered and filtrate was concentrated, diluted with methylene chloride, washed with a saturated aqueous solution of Na2SO3. The organic phase was dried over anhydrous Na2SO4, filtered, and concentrated, followed by the addition of one equivalent HCl in ether to afford (3-8) as white solid (m,z (ES) 534 (MH+)).

Workup

  1. filtrationThe solid was filtered
  2. concentrationfiltrate was concentrated
  3. additiondiluted with methylene chloride
  4. washwashed with a saturated aqueous solution of Na2SO3
  5. dry with materialThe organic phase was dried over anhydrous Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-0d734a9d85d74e79bcad383aef599f76
Source dataset
uspto-grants-2007_10
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07276520B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes