Methanol → Tert-butyl 2-(4-methoxy-4-oxobutyl)piperidine-1-carboxylate

HRID 1881681Notes

Reaction equation

HRID 1881681 reaction equation
[C:1](N1C=CN=C1)(N1C=CN=C1)=O.[C:13]([O:17][C:18]([N:20]1[CH2:25][CH2:24][CH2:23][CH2:22][CH:21]1[CH2:26][CH2:27][CH2:28][C:29]([OH:31])=[O:30])=[O:19])([CH3:16])([CH3:15])[CH3:14].CO>C(Cl)Cl>[CH3:1][O:30][C:29](=[O:31])[CH2:28][CH2:27][CH2:26][CH:21]1[CH2:22][CH2:23][CH2:24][CH2:25][N:20]1[C:18]([O:17][C:13]([CH3:16])([CH3:14])[CH3:15])=[O:19]

Participants

5

Reactant 3

HCID 887MethanolHCID 682631,1'-CarbonyldiimidazoleHCID 579041914-{1-[(tert-Butoxy)carbonyl]piperidin-2-yl}butanoic acid

Product 1

HCID 57904248Tert-butyl 2-(4-methoxy-4-oxobutyl)piperidine-1-carboxylateYield 94%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

1,1′-Carbonyldiimidazole (23.3 g, 143.7 mmol) was added to a solution of 4-(1-tert-butoxycarbonyl)piperidin-2-yl)butanoic acid (2) (26 g, 95.8 mmol) in methylene chloride. The reaction mixture was stirred at room temperature for 1 h. Methanol (19.4 ml, 479 mmol) was then added and the reaction mixture was stirred overnight. The complete reaction was checked by means of TLC. When the reaction was complete, the reaction mixture was washed 3× with sat. NH4Cl solution (aqueous) and 2× with sat. NaCl solution. The organic phase was dried over MgSO4, filtered and concentrated under reduced pressure to obtain tert-butyl 2-(4-methoxy-4-oxobutyl)piperidine-1-carboxylate (3) (25.67 g, 94%).

Workup

  1. stirringthe reaction mixture was stirred overnight
  2. customThe complete reaction
  3. washthe reaction mixture was washed 3× with sat. NH4Cl solution (aqueous) and 2× with sat. NaCl solution
  4. dry with materialThe organic phase was dried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-0a5e6dc1e6bd4e86b3202561764af01e
Source dataset
uspto-grants-2012_11
Patent number
US08318769B2

Reaction notes

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