Sodium Carbonate → HCID 22083372, compound

HRID 2188027Notes

Reaction equation

HRID 2188027 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[CH:5][CH:6]=[C:7]2[C:11]=1[C:10](=[O:12])[N:9]([CH2:13][C@H:14]1[CH2:19][C:18](OCC)([O:20]CC)[CH2:17][CH2:16][N:15]1[C@H:26]([C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1)[CH3:27])[CH2:8]2.C(=O)([O-])[O-].[Na+].[Na+]>FC(F)(F)C(O)=O.O>[CH3:1][O:2][C:3]1[CH:4]=[CH:5][CH:6]=[C:7]2[C:11]=1[C:10](=[O:12])[N:9]([CH2:13][C@H:14]1[CH2:19][C:18](=[O:20])[CH2:17][CH2:16][N:15]1[C@H:26]([C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1)[CH3:27])[CH2:8]2

Participants

5

Reactant 2

HCID 10340Sodium CarbonateHCID 22083371HCID 22083371, compound

Product 1

HCID 22083372HCID 22083372, compoundYield 100.3%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6422Trifluoroacetic acidSolvent

Procedure

2-(R)-(7-Methoxy-2,3-dihydro-isoindol-1-one-2-ylmethyl)-4,4-diethoxy-1(1-(S)-phenyl-ethyl)-piperidine (2.0 g, 4.4 mmol) was dissolved in a ice cold mixture of trifluoroacetic acid and water (10 ml, 9:1) and stirred or 0.5 hour on an ice bath. The reaction mixture was poured on aqueous sodium carbonate (100 ml) and extracted with dichloromethane (2×50 ml). The organic phase was dried (MgSO4), filtered and evaporated in vacuo, affording 1.67 g (100%) of 2-(R)-(7-methoxy-2,3-dihydro-isoindol-1-one-2-ylmethyl)-4-oxo-1(1-(S)-phenyl-ethyl)-piperidine.

Workup

  1. extractionextracted with dichloromethane (2×50 ml)
  2. dry with materialThe organic phase was dried (MgSO4)
  3. filtrationfiltered
  4. customevaporated in vacuo

Sources & evidence

ORD record
ord-5110249eb84942d29c416dfaa40e31fb
Source dataset
uspto-grants-2002_06
Patent number
US06410556B1

Reaction notes

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