Dichloromethane → HCID 117849020, compound

HRID 1477666Notes

Reaction equation

HRID 1477666 reaction equation
ClCCl.[F:4][C:5]1[CH:10]=[CH:9][C:8]([C:11]2(O)[CH2:16][CH2:15][N:14]([C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18])[CH:13]([CH3:24])[CH2:12]2)=[CH:7][CH:6]=1.NS(F)(F)[F:28].C(=O)([O-])[O-].[Na+].[Na+]>C(Cl)(Cl)Cl>[F:28][C:11]1([C:8]2[CH:9]=[CH:10][C:5]([F:4])=[CH:6][CH:7]=2)[CH2:16][CH2:15][N:14]([C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18])[CH:13]([CH3:24])[CH2:12]1

Participants

6

Reactant 4

HCID 6344DichloromethaneHCID 10340Sodium CarbonateHCID 22002676HCID 22002676, compoundHCID 117839862HCID 117839862, compound

Product 1

HCID 117849020HCID 117849020, compoundYield 90.1%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

To a dichloromethane solution (2.0 mL) of tert-butyl 4-(4-fluorophenyl)-4-hydroxy-2-methylpiperidine-1-carboxylate (60.0 mg, 0.194 mmol) synthesized in Reference Synthesis Example 279, bis(2-methoxyethyl))amino-sulfur trifluoride (46.9 mg, 0.291 mmol) was added at −78° C. and the resultant mixture was stirred at room temperature for 1 day. After completion of the reaction, saturated sodium carbonate aqueous solution was added to the reaction solution and extraction from the resultant mixture with chloroform was performed. The organic layer was dried over anhydrous sodium sulfate and concentrated under reduced pressure to obtain a crude product (54.4 mg) of the title compound.

Workup

  1. additionwas added at −78° C.
  2. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  3. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-96accc008401461f90c2390028a0d32f
Source dataset
uspto-grants-2016_08
Patent number
US09403798B2

Reaction notes

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