HCID 68817252, compound → HCID 68817179, compound

HRID 736798Notes

Reaction equation

HRID 736798 reaction equation
C([O:8][C:9]1[CH:14]=[CH:13][C:12]([S:15]([NH:18][C@@H:19]2[CH2:24][CH2:23][N:22]([C:25]([O:27][C:28]([CH3:31])([CH3:30])[CH3:29])=[O:26])[CH2:21][C@:20]2([CH3:36])[C:32]([O:34][CH3:35])=[O:33])(=[O:17])=[O:16])=[CH:11][CH:10]=1)C1C=CC=CC=1>CO.[OH-].[OH-].[Pd+2]>[OH:8][C:9]1[CH:10]=[CH:11][C:12]([S:15]([NH:18][C@@H:19]2[CH2:24][CH2:23][N:22]([C:25]([O:27][C:28]([CH3:29])([CH3:30])[CH3:31])=[O:26])[CH2:21][C@:20]2([CH3:36])[C:32]([O:34][CH3:35])=[O:33])(=[O:16])=[O:17])=[CH:13][CH:14]=1

Participants

4

Reactant 1

HCID 68817252HCID 68817252, compound

Product 1

HCID 68817179HCID 68817179, compoundYield 96%

Reagents, catalysts & solvents 2

HCID 9942167Palladium hydroxideCatalystHCID 887MethanolSolvent

Procedure

(3S,4R)-1-tert-Butyl 3-methyl 4-(4-(benzyloxy)phenylsulfonamido)-3-methylpiperidine-1,3-dicarboxylate (4.659 g, 8.09 mmol) was taken up in methanol (30 mL) and combined with Pearlman's catalyst (501 mg). The heterogeneous mixture was stirred under a hydrogen atmosphere for 0.5 h, and then filtered through celite and concentrated to give (3S,4R)-1-tert-butyl 3-methyl 4-(4-hydroxyphenylsulfonamido)-3-methylpiperidine-1,3-dicarboxylate (3.754 g, 7.73 mmol, 96%) as a colorless solid. 1H NMR (400 MHz, CHLOROFORM-D) δ ppm 1.16 (s, 3H) 1.24 (s, 9H) 1.37-1.48 (m, 10H) 1.68-1.77 (m, 2H) 2.54 (d, J=15.41 Hz, 1 H) 2.82 (td, J=13.20, 2.65 Hz, 1H) 3.27 (ddd, J=12.25, 8.59, 3.92 Hz, 1H) 4.00 (ddd, J=13.58, 2.53, 2.34 Hz, 1H) 4.33 (d, J=13.89 Hz, 1H) 6.85-6.89 (m, 2H) 7.67-7.72 (m, 2H).

Workup

  1. filtrationfiltered through celite and
  2. concentrationconcentrated

Sources & evidence

ORD record
ord-8cf3a1c26caf4553998f43be3d181569
Source dataset
uspto-grants-2009_09
Patent number
US07595327B2

Reaction notes

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