Triethylamine → 1-Ethoxycarbonyl-4-methyloxypiperidine

HRID 1039599

Reaction equation

HRID 1039599 reaction equation
[CH2:1]([O:3][C:4]([N:6]1[CH2:11][CH2:10][CH:9]([OH:12])[CH2:8][CH2:7]1)=[O:5])[CH3:2].[CH2:13](N(CC)CC)C.CS(Cl)(=O)=O>C(OCC)(=O)C>[CH2:1]([O:3][C:4]([N:6]1[CH2:7][CH2:8][CH:9]([O:12][CH3:13])[CH2:10][CH2:11]1)=[O:5])[CH3:2]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 96394Ethyl 4-hydroxypiperidine-1-carboxylate

Product 1

HCID 451201911-Ethoxycarbonyl-4-methyloxypiperidine

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
3 °C

Procedure

1-ethoxycarbonyl-4-hydroxypiperidine (30.3 g) and triethylamine (23 g) were dissolved in ethyl acetate (182 mL) and the obtained mixture was cooled to 3° C. Methanesulfonyl chloride (22.05 g) was added thereto under stirring while taking caution such that the temperature did not exceed 20° C., and the mixture was continuously stirred under ice cooling for 1 hour. The obtained reaction mixture was washed with water (90 mL×3). The organic layer was isolated and concentrated to obtain a target compound as a light yellow oily substance. The yield amount was 43.09 g (98%).

Workup

  1. customdid not exceed 20° C.
  2. stirringthe mixture was continuously stirred under ice cooling for 1 hour
  3. customThe obtained reaction mixture
  4. washwas washed with water (90 mL×3)
  5. customThe organic layer was isolated
  6. concentrationconcentrated
  7. customto obtain a target compound as a light yellow oily substance

Sources & evidence

ORD record
ord-46653c60c6b244bfafb34f1aaeb28f08
Source dataset
uspto-grants-2013_10
Patent number
US08552188B2

Linked notes

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