Triethylamine → N-Boc-3-mesyloxypiperidine

HRID 1465714Notes

Reaction equation

HRID 1465714 reaction equation
[OH:1][CH:2]1[CH2:7][CH2:6][CH2:5][N:4]([C:8]([O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[O:9])[CH2:3]1.C(N(CC)CC)C.[CH3:22][S:23](Cl)(=[O:25])=[O:24]>ClCCl.CN(C1C=CN=CC=1)C>[CH3:22][S:23]([O:1][CH:2]1[CH2:7][CH2:6][CH2:5][N:4]([C:8]([O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[O:9])[CH2:3]1)(=[O:25])=[O:24]

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 5456991-Boc-3-hydroxypiperidine

Product 1

HCID 568122N-Boc-3-mesyloxypiperidineYield 109.4%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

Tert-butyl 3-hydroxypiperidine-1-carboxylate (3.6 g, 18 mmol) was dissolved in dichloromethane (20 mL) and cooled to 0° C., triethylamine (4 mL) was added, followed by dropwise addition of methanesulfonyl chloride (2.28 g, 20 mmol) and DMAP (10 mg). The reaction mixture was warmed to room temperature and stirred overnight. The reaction mixture was quenched with saturated NaHCO3, and extracted with dichloromethane. The organic layer was washed with H2O, dried and concentrated to give crude product (5.5 g).

Workup

  1. temperatureThe reaction mixture was warmed to room temperature
  2. customThe reaction mixture was quenched with saturated NaHCO3
  3. extractionextracted with dichloromethane
  4. washThe organic layer was washed with H2O
  5. customdried
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-1bba5f034eba49639ce183da1bb7523b
Source dataset
uspto-grants-2015_04
Patent number
US08999966B2

Reaction notes

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