Sodium Hydroxide → HCID 89649628, compound

HRID 1479015Notes

Reaction equation

HRID 1479015 reaction equation
[OH-].[Na+].[C:3]([O:7][C:8]([N:10]1[CH2:15][CH2:14][C:13](=[CH:16][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=2[C:23]([O:25]C)=[O:24])[CH2:12][CH2:11]1)=[O:9])([CH3:6])([CH3:5])[CH3:4]>CCO>[C:3]([O:7][C:8]([N:10]1[CH2:15][CH2:14][C:13](=[CH:16][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=2[C:23]([OH:25])=[O:24])[CH2:12][CH2:11]1)=[O:9])([CH3:6])([CH3:4])[CH3:5]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 69841045HCID 69841045, compound

Product 1

HCID 89649628HCID 89649628, compoundYield 94.5%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

1M NaOH (2 mL; 2 mmol; 6.63 eq.) was added to a solution of 4-(2-methoxycarbonyl-benzylidene)-piperidine-1-carboxylic acid tert-butyl ester (100 mg; 0.30 mmol; 1 eq.) in EtOH (2 mL) and the reaction mixture was stirred at room temperature for 16 hours then concentrated in vacuo. The residue was partitioned between DCM and 1M HCl and the two phases separated. The aqueous layer was extracted with DCM and the combined organic layers were dried over magnesium sulfate and concentrated in vacuo to afford the title compound (90 mg, 94%) as a white solid. HPLC (max plot) 98.9%; Rt 4.37 min. UPLC/MS: (MS−) 316.4 ([M−H]−).

Workup

  1. concentrationthen concentrated in vacuo
  2. customThe residue was partitioned between DCM and 1M HCl
  3. customthe two phases separated
  4. extractionThe aqueous layer was extracted with DCM
  5. dry with materialthe combined organic layers were dried over magnesium sulfate
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-40cb8f91c6154ef6bb567b2a352d209b
Source dataset
uspto-grants-2016_08
Patent number
US09403835B2

Reaction notes

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