1,1'-Carbonyldiimidazole → Tert-butyl 4-(methoxy(methyl)carbamoyl)-3-methylpiperidine-1-carboxylate

HRID 1806097Notes

Reaction equation

HRID 1806097 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([C:14]([OH:16])=O)[CH:10]([CH3:17])[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].N1(C(N2C=CN=C2)=O)C=CN=C1.Cl.[CH3:31][O:32][NH:33][CH3:34]>C(Cl)Cl>[CH3:31][O:32][N:33]([CH3:34])[C:14]([CH:11]1[CH2:12][CH2:13][N:8]([C:6]([O:5][C:1]([CH3:2])([CH3:3])[CH3:4])=[O:7])[CH2:9][CH:10]1[CH3:17])=[O:16]

Participants

5

Reactant 3

HCID 682631,1'-CarbonyldiimidazoleHCID 81138Methanamine, N-methoxy-, hydrochloride (1:1)HCID 4248616N-Boc-3-methyl-4-piperidinecarboxylic acid

Product 1

HCID 86601647Tert-butyl 4-(methoxy(methyl)carbamoyl)-3-methylpiperidine-1-carboxylateYield 65%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 1-(tert-butoxycarbonyl)-3-methylpiperidine-4-carboxylic acid (3.00 g, 12.3 mmol) in CH2Cl2 (200 mL) was added di(1H-imidazol-1-yl)methanone (2.19 g, 13.6 mmol) portionwise. After the bubbling ceased (˜60 minutes), N-methoxymethanamine hydrochloride (1.32 g, 13.6 mmol) was added in one portion. The mixture was allowed to stir overnight at ambient temperature, then was washed with water, 1N HCl, and saturated sodium bicarbonate. The organic layer was dried, filtered, and concentrated to give the desired product (2.29 g, 64.8% yield) as a colorless oil.

Workup

  1. additionwas added in one portion
  2. washwas washed with water, 1N HCl, and saturated sodium bicarbonate
  3. customThe organic layer was dried
  4. filtrationfiltered
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-f6ca1f75eef54e3281ddbbada9b2ebf1
Source dataset
uspto-grants-2013_01
Patent number
US08354540B2

Reaction notes

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