Hydrochloric Acid → (R)-Pyrrolidine-2-carboxylic acid (4-hydroxy-phenyl)-amide

HRID 1474507Notes

Reaction equation

HRID 1474507 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.OC1C=CC(NC([C@@H]2CCCN2)=O)=CC=1.Cl>C(O)(C)C>[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 3

HCID 313Hydrochloric AcidHCID 11390123(S)-Pyrrolidine-2-carboxylic acid (4-hydroxy-phenyl)-amideHCID 68477807HCID 68477807, compound

Product 1

HCID 11229515(R)-Pyrrolidine-2-carboxylic acid (4-hydroxy-phenyl)-amide

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent2×

Procedure

This compound was prepared from (R)-2-(4-benzyloxy-phenylcarbamoyl)-pyrrolidine-1-carboxylic acid benzyl ester, using the same method used to prepare (S)-pyrrolidine-2-carboxylic acid (4-hydroxy-phenyl)-amide. The free base was dissolved in hot isopropanol (20 mL) and treated with a saturated solution of hydrogen chloride in isopropanol (3 mL). The product crystallized as the hydrochloride salt, 2.43 g (59% for 2 steps). MS m/z 207 (MH+). 1H NMR(DMSO-d6) δ 1.93 (m, 3H), 2.39 (m, 1H), 3.26 (m, 2H), 4.35 (t, 1H), 6.76 (d, 2H), 7.43 (d, 2H), 9.43 (br s, 1H) and 10.70 (s, 1H). Anal. calcd for C11H14N2O2: C, 54.44; H, 6.23; N, 11.54. Found: C, 54.33; H, 6.26; N, 11.57.

Workup

  1. customThe product crystallized as the hydrochloride salt, 2.43 g (59% for 2 steps)

Sources & evidence

ORD record
ord-d593318454a9418993b4391c2c6e162d
Source dataset
uspto-grants-2015_04
Patent number
US09018241B2

Reaction notes

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