Pyridine → (2S,5R)-tert-butyl 5-(N-(benzyloxy)-2-nitrophenylsulfonamido)-2-cyanopiperidine-1-carboxylate

HRID 1406856Notes

Reaction equation

HRID 1406856 reaction equation
N1C=CC=CC=1.[CH2:7]([O:14][N:15]([C@H:28]1[CH2:33][N:32]([C:34]([O:36][C:37]([CH3:40])([CH3:39])[CH3:38])=[O:35])[C@H:31]([C:41](=O)[NH2:42])[CH2:30][CH2:29]1)[S:16]([C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=1[N+:25]([O-:27])=[O:26])(=[O:18])=[O:17])[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1.O(S(C(F)(F)F)(=O)=O)S(C(F)(F)F)(=O)=O.CCOC(C)=O>C1COCC1>[CH2:7]([O:14][N:15]([C@H:28]1[CH2:33][N:32]([C:34]([O:36][C:37]([CH3:38])([CH3:40])[CH3:39])=[O:35])[C@H:31]([C:41]#[N:42])[CH2:30][CH2:29]1)[S:16]([C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=1[N+:25]([O-:27])=[O:26])(=[O:18])=[O:17])[C:8]1[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=1

Participants

6

Reactant 4

HCID 1049PyridineHCID 8857Ethyl AcetateHCID 67749Trifluoromethanesulfonic anhydrideHCID 86700668(2S,5R)-tert-butyl 5-(N-(benzyloxy)-2-nitrophenylsulfonamido)-2-carbamoyl-piperidine-1-carboxylate

Product 1

HCID 86700670(2S,5R)-tert-butyl 5-(N-(benzyloxy)-2-nitrophenylsulfonamido)-2-cyanopiperidine-1-carboxylateYield 79%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Pyridine (2 mL) was added to a solution of (2S,5R)-tert-butyl 5-(N-(benzyloxy)-2-nitrophenylsulfonamido)-2-carbamoylpiperidine-1-carboxylate (1.0 g, 1.87 mmol) in dry THF (40 mL). Then, Tf2O (1.0 mL) was slowly added over 5 minutes. The mixture was stiffed at 0° C. for 1 h and then EtOAc (30 mL) was added. The mixture was washed with saturated sodium chloride (4×), dried overNa2SO4, and concentrated. The residue was purified by silica gel column chromatography (gradient elution 0˜40% petroleum ether/EtOAc) to give (2S,5R)-tert-butyl 5-(N-(benzyloxy)-2-nitrophenylsulfonamido)-2-cyanopiperidine-1-carboxylate (0.76 g, 79%) as a yellow solid ESI-MS (EI+, m/z): 539.0 [M+Na]+.

Workup

  1. washThe mixture was washed with saturated sodium chloride (4×)
  2. customdried overNa2SO4, and
  3. concentrationconcentrated
  4. customThe residue was purified by silica gel column chromatography (gradient elution 0˜40% petroleum ether/EtOAc)

Sources & evidence

ORD record
ord-0a3cc6624b5d4963bf2e8e6d3ce7bc8a
Source dataset
uspto-grants-2014_12
Patent number
US08916709B2

Reaction notes

Loading…