HCID 68480254, compound → (S)-Pyrrolidine-2-carboxylic acid (4-hydroxy-phenyl)-amide

HRID 1474505Notes

Reaction equation

HRID 1474505 reaction equation
C(OC([N:11]1[CH2:15][CH2:14][CH2:13][C@H:12]1[C:16](=[O:32])[NH:17][C:18]1[CH:23]=[CH:22][C:21]([O:24]CC2C=CC=CC=2)=[CH:20][CH:19]=1)=O)C1C=CC=CC=1.[H][H]>C(O)C.O.[Pd]>[OH:24][C:21]1[CH:20]=[CH:19][C:18]([NH:17][C:16]([C@@H:12]2[CH2:13][CH2:14][CH2:15][NH:11]2)=[O:32])=[CH:23][CH:22]=1

Participants

5

Reactant 2

HCID 68480254HCID 68480254, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 11390123(S)-Pyrrolidine-2-carboxylic acid (4-hydroxy-phenyl)-amide

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 19096565Water ethanolSolvent

Procedure

A suspension of (S)-2-(4-benzyloxy-phenylcarbamoyl)-pyrrolidine-1-carboxylic acid benzyl ester (7.0 g, 16.3 mmol) in ethanol/water (70 mL/7 mL) was hydrogenated over 10% palladium on carbon (0.41 g) at 55 psi of hydrogen, at 50° C., for 5 hours. The mixture was cooled, and the catalyst was removed by filtration. The solvent was evaporated in vacuo. The residue was dissolved in hot ethanol (30 mL) and treated with a saturated solution of hydrogen chloride in ethanol (3 mL). The product crystallized as the hydrochloride salt, 1.27 g (32%), a colorless solid. MS m/z 207 (MH+). 1H NMR(DMSO-d6) δ 1.92 (m, 3H), 2.43 (m, 1H), 3.28 (m, 2H), 4.31 (m, 1H), 6.77 (d, 2H), 7.47 (d, 2H), 9.44 (br s, 1H) and 10.75 (s, 1H). Anal. calcd for C11H14N2O2: C, 54.44; H, 6.23; N, 11.54. Found: C, 54.28; H, 6.06; N, 11.66.

Workup

  1. temperatureThe mixture was cooled
  2. customthe catalyst was removed by filtration
  3. customThe solvent was evaporated in vacuo
  4. dissolutionThe residue was dissolved in hot ethanol (30 mL)
  5. additiontreated with a saturated solution of hydrogen chloride in ethanol (3 mL)
  6. customThe product crystallized as the hydrochloride salt, 1.27 g (32%)

Sources & evidence

ORD record
ord-7bec20dadb234a60acafe7531b0470dd
Source dataset
uspto-grants-2015_04
Patent number
US09018241B2

Reaction notes

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