1,1'-Carbonyldiimidazole → tert-Butyl 4-(methoxy(methyl)carbamoyl)piperidine-1-carboxylate

HRID 1972803Notes

Reaction equation

HRID 1972803 reaction equation
[C:1]([N:8]1[CH2:13][CH2:12][CH:11]([C:14]([OH:16])=O)[CH2:10][CH2:9]1)([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2].C1N=CN(C(N2C=NC=C2)=O)C=1.Cl.[CH3:30][NH:31][O:32][CH3:33]>C1COCC1.CCOC(C)=O>[C:4]([O:3][C:1]([N:8]1[CH2:9][CH2:10][CH:11]([C:14](=[O:16])[N:31]([O:32][CH3:33])[CH3:30])[CH2:12][CH2:13]1)=[O:2])([CH3:5])([CH3:6])[CH3:7]

Participants

6

Reactant 3

HCID 682631,1'-CarbonyldiimidazoleHCID 81138Methanamine, N-methoxy-, hydrochloride (1:1)HCID 3928711-(tert-Butoxycarbonyl)-4-piperidinecarboxylic acid

Product 1

HCID 11065582tert-Butyl 4-(methoxy(methyl)carbamoyl)piperidine-1-carboxylate

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

N-BOC-piperidine-4-carboxylic acid (3.00 g, 13.08 mmol) was dissolved in THF and CDI (4.00 g, 24.7 mmol) was added in portions. The mixture was stirred for 2 h and N,O-dimethylhydroxylamine hydrochloride (4.00 g, 41 mmol) was added and stirring continued for 12 hours. The mixture was diluted with EtOAc and extracted 3 times with brine, dried over Na2SO4, filtered and concentrated in vacuo. The residue was purified Biotage® to provide the title compound. 1H NMR (CD2Cl2) δ 4.12 (d,2H), 3.71 (s, 3H), 3.15 (s, 3H), 2.83 (m, 1H), 2.76 (t, 2H), 1.70 (dd, 2H), 1.59 (m, 2H), 1.45 (s, 9H).

Workup

  1. stirringstirring
  2. waitcontinued for 12 hours
  3. extractionextracted 3 times with brine
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customThe residue was purified Biotage®

Sources & evidence

ORD record
ord-5ae63fca4e5a49819ba3249478eb2f09
Source dataset
uspto-grants-2013_04
Patent number
US08431695B2

Reaction notes

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