2-Dimethylaminopyridine → t-butyl (S)-3-isobutyroxymethyl-1-piperidinecarboxylate

HRID 1081206Notes

Reaction equation

HRID 1081206 reaction equation
CN(C1C=CC=CN=1)C.[OH:10][CH2:11][C@H:12]1[CH2:17][CH2:16][CH2:15][N:14]([C:18]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19])[CH2:13]1.[C:25](Cl)(=[O:29])[CH:26]([CH3:28])[CH3:27]>N1C=CC=CC=1>[C:25]([O:10][CH2:11][C@H:12]1[CH2:17][CH2:16][CH2:15][N:14]([C:18]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19])[CH2:13]1)(=[O:29])[CH:26]([CH3:28])[CH3:27]

Participants

5

Reactant 3

HCID 218852-DimethylaminopyridineHCID 62325Isobutyryl chlorideHCID 1514448tert-Butyl (3S)-3-(hydroxymethyl)piperidine-1-carboxylate

Product 1

HCID 54001268t-butyl (S)-3-isobutyroxymethyl-1-piperidinecarboxylate

Reagents, catalysts & solvents 1

HCID 1049PyridineCatalyst

Procedure

170 mg of dimethylaminopyridine and 3.4 mg of pyridine are added to 3.0 g of t-butyl (S)-3-hydroxymethyl-1-piperidinecarboxylate. 1.66 ml of isobutyryl chloride are added dropwise thereto. The reaction mixture is then concentrated. The residue is taken up in ether and the ether phase is washed in succession with 20 ml of citric acid, water, sodium bicarbonate solution and water. After drying and evaporation of the ether phase there are obtained 3.9 g of t-butyl (S)-3-isobutyroxymethyl-1-piperidinecarboxylate, Rf=0.87 (ether). 3.09 g of this ester are dissolved in 80 ml of methylene chloride and treated with 20 ml of trifluoroacetic acid. After stirring for 30 minutes the solution is concentrated. 30 ml of methanol are added to the residue and saturated sodium bicarbonate solution is then added dropwise. The aqueous phase is extracted with methylene chloride and the methylene chloride extracts are dried and concentrated. There are obtained 2.82 g of (S)-3-isobutyroxymethyl-1-piperidinecarboxylic acid trifluoroacetic acid salt, Rf=0.4 (Takeda solution).

Workup

  1. concentrationThe reaction mixture is then concentrated
  2. washthe ether phase is washed in succession with 20 ml of citric acid, water, sodium bicarbonate solution and water
  3. customAfter drying
  4. customevaporation of the ether phase

Sources & evidence

ORD record
ord-5845ecb261af4b34b009f8b5d1acca9c
Source dataset
uspto-grants-1996_12
Patent number
US05583133

Reaction notes

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