Triethylamine → Benzyl 4-((methanesulfonyl)oxy)piperidine-1-carboxylate

HRID 1676192Notes

Reaction equation

HRID 1676192 reaction equation
[OH:1][CH:2]1[CH2:7][CH2:6][N:5]([C:8]([O:10][CH2:11][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)=[O:9])[CH2:4][CH2:3]1.C(N(CC)CC)C.[CH3:25][S:26](Cl)(=[O:28])=[O:27]>C(Cl)Cl>[CH3:25][S:26]([O:1][CH:2]1[CH2:3][CH2:4][N:5]([C:8]([O:10][CH2:11][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)=[O:9])[CH2:6][CH2:7]1)(=[O:28])=[O:27]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 2794620Benzyl 4-Hydroxy-1-piperidinecarboxylate

Product 1

HCID 58303455Benzyl 4-((methanesulfonyl)oxy)piperidine-1-carboxylateYield 107.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

To benzyl 4-hydroxypiperidine-1-carboxylate (48.8 g, 207 mmol) in CH2Cl2 (400 mL) was added triethylamine (57.8 mL, 415 mmol), the mixture was cooled to 0° C. under nitrogen and then methanesulfonyl chloride (17.78 mL, 228 mmol) was added over 15 minutes keeping internal temperature below 30° C. After 2 hours at 0° C., the reaction was quenched with 300 mL of 0.1 N aqueous HCl, the organic layer was washed with 300 mL of water, 300 mL of brine, dried with MgSO4, filtered and concentrated to give the product (69.5 g) as an amber liquid which was used without further purification. MS (ESI) 314.4 (M+1).

Workup

  1. customtemperature below 30° C
  2. customthe reaction was quenched with 300 mL of 0.1 N aqueous HCl
  3. washthe organic layer was washed with 300 mL of water, 300 mL of brine
  4. dry with materialdried with MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-386cb040920b461b90d620e0d630ece5
Source dataset
uspto-grants-2011_08
Patent number
US08003796B2

Reaction notes

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