HCID 54392286, compound → HCID 53738387, compound

HRID 343626Notes

Reaction equation

HRID 343626 reaction equation
C([O:8][NH:9][C:10]([C@H:12]1[C@@H:17]([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[CH:16]=[CH:15][CH2:14][N:13]1[S:24]([C:27]1[CH:32]=[CH:31][C:30]([O:33][CH3:34])=[CH:29][CH:28]=1)(=[O:26])=[O:25])=[O:11])C1C=CC=CC=1>C(O)C.[Pd]>[OH:8][NH:9][C:10]([C@H:12]1[C@@H:17]([C:18]2[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=2)[CH2:16][CH2:15][CH2:14][N:13]1[S:24]([C:27]1[CH:28]=[CH:29][C:30]([O:33][CH3:34])=[CH:31][CH:32]=1)(=[O:26])=[O:25])=[O:11]

Participants

4

Reactant 1

HCID 54392286HCID 54392286, compound

Product 1

HCID 53738387HCID 53738387, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

To a solution of (+)-(2R*-3R*)-N-benzyloxy-1-(4-methoxybenzenesulfonyl)-3-phenyl-1,2,3,6tetrahydropyridine-2-carboxamide (35 mg, 0.073 mmol) in ethanol (5 ml) is added 10% palladium on carbon (10 mg, 5 mol). The flask is evacuated and backfilled with hydrogen (repeated two times). The reaction mixture is then stirred for 1 hour at which time it is filtered through Celite™ and concentrated. The product (+)-2R*-3R*)-N-hydroxy-1-(4-methoxybenzenesulfonyl)-3-phenylpiperidine-2-carboxamide was collected as a white solid. Melting point 163° C. (dec). Mass spectrum [PBMS w/C.I. (NH3)]: m/Z 390 (m+H2), (m+NH4). 1H NMR (CD3OD) δ7.73 (d, J=8.9 Hz, 2 H), 7.31-737 (m, 5 H), 7.04 (d, 8.9 Hz, 2 H0, 4.89 (s, H2O), 4.34 (d, J=5.4 Hz,1 H), 3.86 (s, 3 H), 3.74-3.63 (m, 2 H), 3.31 (bs, CD3OD), 2.99-2.90 (m, 1 H), 2.58-2.52 (m, 1 H), 1.94-1.88 (m, 1 H), 1.67-160 (m, 2 H).

Workup

  1. customThe flask is evacuated
  2. filtrationis filtered through Celite™
  3. concentrationconcentrated
  4. customThe product (+)-2R*-3R*)-N-hydroxy-1-(4-methoxybenzenesulfonyl)-3-phenylpiperidine-2-carboxamide was collected as a white solid

Sources & evidence

ORD record
ord-60f75021f15b44508247d86026b89d3a
Source dataset
uspto-grants-1999_01
Patent number
US05861510

Reaction notes

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