Potassium Carbonate → HCID 69063371, compound

HRID 734765Notes

Reaction equation

HRID 734765 reaction equation
[F:1][C:2]([F:22])([F:21])[CH:3]([CH:5]1[CH2:10][CH2:9][N:8]([C:11]([O:13][CH2:14][C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)=[O:12])[CH2:7][CH2:6]1)[OH:4].CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O.C(=O)([O-])[O-].[K+].[K+]>C(Cl)Cl>[F:22][C:2]([F:1])([F:21])[C:3]([CH:5]1[CH2:10][CH2:9][N:8]([C:11]([O:13][CH2:14][C:15]2[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=2)=[O:12])[CH2:7][CH2:6]1)=[O:4]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 159087TriacetoxyperiodinaneHCID 67403017HCID 67403017, compound

Product 1

HCID 69063371HCID 69063371, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of 1.00 g (83.15 mmol) of benzyl 4-(2,2,2-trifluoro-1-hydroxyethyl)piperidine-1-carboxylate and 4.95 g (11.66 mmol) Dess-Martin periodinane in 30 mL of DCM was stirred for 20 hours at RT and then made alkaline with saturated aqueous potassium carbonate solution. The reaction mixture was filtered and the phases of the filtrate were separated. The organic phase was dried over sodium sulfate and evaporated down in vacuo. Yield: 896 mg (90% of theoretical); C15H16F3NO3 (M=315.288); calc.: molpeak (M−H)−: 314; found: molpeak (M−H)−: 314; Rf value: 0.39 (silica gel, cyc/EtOAc 2: 1).

Workup

  1. filtrationThe reaction mixture was filtered
  2. customthe phases of the filtrate were separated
  3. dry with materialThe organic phase was dried over sodium sulfate
  4. customevaporated down in vacuo

Sources & evidence

ORD record
ord-ed4523e256924a92b3b60d16d62988c3
Source dataset
uspto-grants-2009_09
Patent number
US07592358B2

Reaction notes

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