Sodium Hydroxide → HCID 53435658, compound

HRID 2178500Notes

Reaction equation

HRID 2178500 reaction equation
[OH-].[Na+].C[O:4][C:5]([C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=1[CH:13]1[CH2:17][CH2:16][N:15]([C:18]([O-:20])=[O:19])[CH2:14]1)=[O:6]>CO>[C:7]([O:20][C:18]([N:15]1[CH2:16][CH2:17][CH:13]([C:8]2[CH:9]=[CH:10][CH:11]=[CH:12][C:7]=2[C:5]([OH:4])=[O:6])[CH2:14]1)=[O:19])([CH3:12])([CH3:8])[CH3:5]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 131733027HCID 131733027, compound

Product 1

HCID 53435658HCID 53435658, compoundYield 195.6%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
65 °C

Procedure

NaOH 5M (7.7 ml, 38.6 mmol, 2 eq) is added to a stirred solution of 3-[2-(methoxycarbonyl)phenyl]pyrrolidine-1-carboxylate a1-2 (5.9 g, 19.3 mmol, 1 eq) in MeOH (50 ml) at 65° C. The reaction mixture is stirred overnight at 65° C., then evaporated under vacuum and water (40 ml) is added. The resulting mixture is extracted with ethyl acetate/ethanol (100 ml/10 ml) and again with ethyl acetate (100 ml). The combined organic layers are dried over MgSO4, filtered off and evaporated under vacuum to afford 5.5 g of pure 2-[1-(tert-butoxycarbonyl)pyrrolidin-3-yl]benzoic acid a1-3.

Workup

  1. customevaporated under vacuum and water (40 ml)
  2. additionis added
  3. extractionThe resulting mixture is extracted with ethyl acetate/ethanol (100 ml/10 ml) and again with ethyl acetate (100 ml)
  4. dry with materialThe combined organic layers are dried over MgSO4
  5. filtrationfiltered off
  6. customevaporated under vacuum

Sources & evidence

ORD record
ord-40af9fc67e1544149d360bb45a916143
Source dataset
uspto-grants-2015_06
Patent number
US09067930B2

Reaction notes

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