4-(tert-butoxycarbonylamino-methyl)-benzoic acid (3S,4S)-4-[2-(4-benzyl-3-hydroxy-piperidin-1-yl)-ethanesulfonyl]-phenyl ester → 4-aminomethyl-benzoic acid (3S,4S)-4-[2-(4-benzyl-3-hydroxy-piperidin-1-yl)-ethanesulfonyl]-phenyl ester

HRID 2187098Notes

Reaction equation

HRID 2187098 reaction equation
[CH2:1]([C@H:8]1[CH2:13][CH2:12][N:11]([CH2:14][CH2:15][S:16]([C:19]2[CH:24]=[CH:23][C:22]([O:25][C:26](=[O:42])[C:27]3[CH:32]=[CH:31][C:30]([CH2:33][NH:34]C(OC(C)(C)C)=O)=[CH:29][CH:28]=3)=[CH:21][CH:20]=2)(=[O:18])=[O:17])[CH2:10][C@H:9]1[OH:43])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1>C(O)(C(F)(F)F)=O>[CH2:1]([C@H:8]1[CH2:13][CH2:12][N:11]([CH2:14][CH2:15][S:16]([C:19]2[CH:24]=[CH:23][C:22]([O:25][C:26](=[O:42])[C:27]3[CH:28]=[CH:29][C:30]([CH2:33][NH2:34])=[CH:31][CH:32]=3)=[CH:21][CH:20]=2)(=[O:17])=[O:18])[CH2:10][C@H:9]1[OH:43])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

3

Reactant 1

HCID 865847964-(tert-butoxycarbonylamino-methyl)-benzoic acid (3S,4S)-4-[2-(4-benzyl-3-hydroxy-piperidin-1-yl)-ethanesulfonyl]-phenyl ester

Product 1

HCID 101857994-aminomethyl-benzoic acid (3S,4S)-4-[2-(4-benzyl-3-hydroxy-piperidin-1-yl)-ethanesulfonyl]-phenyl esterYield 67%

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

A solution of 200 mg 4-(tert-butoxycarbonylamino-methyl)-benzoic acid (3S,4S)-4-[2-(4-benzyl-3-hydroxy-piperidin-1-yl)-ethanesulfonyl]-phenyl ester in 3.8 ml TFA was stirred for 1 hour at 0° C. The solvent was removed under reduced pressure and the crude product was diluted in diethylether and 3 drops of a saturated HCl-solution in diethylether were added. Filtration yielded 120 mg (0.22 mmol, 67%) 4-aminomethyl-benzoic acid (3S,4S)-4-[2-(4-benzyl-3-hydroxy-piperidin-1-yl)-ethanesulfonyl]-phenyl ester; hydrochloride(1:2) as colorless crystalls.

Workup

  1. customThe solvent was removed under reduced pressure
  2. additionthe crude product was diluted in diethylether
  3. addition3 drops of a saturated HCl-solution in diethylether were added
  4. filtrationFiltration

Sources & evidence

ORD record
ord-0c27188a72774d6bb990d0582f424a74
Source dataset
uspto-grants-2002_06
Patent number
US06407235B1

Reaction notes

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