3-Methylpiperidine → HCID 86650118, compound

HRID 2179752Notes

Reaction equation

HRID 2179752 reaction equation
CC1C=CC(S(O[CH2:12][C@H:13]2[CH2:17][CH2:16][C@@H:15]([NH:18][C:19]([O:21][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:20])[CH2:14]2)(=O)=O)=CC=1.[CH3:26][CH:27]1[CH2:32][CH2:31][CH2:30][NH:29][CH2:28]1>C(Cl)Cl>[CH3:26][CH:27]1[CH2:32][CH2:31][CH2:30][N:29]([CH2:12][C@H:13]2[CH2:17][CH2:16][C@@H:15]([NH:18][C:19](=[O:20])[O:21][C:22]([CH3:23])([CH3:24])[CH3:25])[CH2:14]2)[CH2:28]1

Participants

4

Reactant 2

HCID 790813-MethylpiperidineHCID 86650113HCID 86650113, compound

Product 1

HCID 86650118HCID 86650118, compoundYield 72.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

To a stirred solution of ((1S,3R)-3-(tert-butoxycarbonylamino)cyclopentyl)methyl 4-methylbenzenesulfonate (Intermediate 18-step 2, about 0.5 g) in DCM (50 ml) potassium carbonate (about 0.3 g) was added at room temperature and cooled to about 0° C. After ten minutes, 3-methylpiperidine (0.21 g) was added and stirred the reaction at room temperature for about 6 hours and completion of the reaction was monitored by TLC. The reaction mixture was neutralized and extracted with DCM, the organic layer was dried over Na2SO4 and concentrated under reduced pressure to furnish the title compound (0.29 g) as a pale yellow solid. 1H NMR (300 MHz, CDCl3: 1.08-1.09 (m, 3H); 1.24-1.29 (m, 1H); 1.39-1.40 (s, 9H); 2.29-2.60 (m, 6H); 2.79-2.80 (m, 8H); 3.70-3.73 (m, 4H); ES Mass: 297 (100%), [M+1].

Workup

  1. waitAfter ten minutes
  2. customthe reaction at room temperature for about 6 hours
  3. extractionextracted with DCM
  4. dry with materialthe organic layer was dried over Na2SO4
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-7de47d0ecb0340b08462122af95004a4
Source dataset
uspto-grants-2015_06
Patent number
US09067966B2

Reaction notes

Loading…