Tetrahydrofuran → 1-(tert-Butoxycarbonyl)-4-(methanesulfonyloxy)piperidine

HRID 1427008Notes

Reaction equation

HRID 1427008 reaction equation
[CH3:1][S:2](Cl)(=[O:4])=[O:3].C(N(CC)CC)C.[OH:13][CH:14]1[CH2:19][CH2:18][N:17]([C:20]([O:22][C:23]([CH3:26])([CH3:25])[CH3:24])=[O:21])[CH2:16][CH2:15]1.O1CCCC1>C(OCC)(=O)C.O>[CH3:1][S:2]([O:13][CH:14]1[CH2:15][CH2:16][N:17]([C:20]([O:22][C:23]([CH3:26])([CH3:25])[CH3:24])=[O:21])[CH2:18][CH2:19]1)(=[O:4])=[O:3]

Participants

7

Reactant 4

HCID 8028TetrahydrofuranHCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 643502Tert-butyl 4-hydroxypiperidine-1-carboxylate

Product 1

HCID 41848691-(tert-Butoxycarbonyl)-4-(methanesulfonyloxy)piperidineYield 95.1%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Procedure

Commercially available methanesulfonyl chloride (6.35 mL, 82.0 mmol) and triethylamine (26.0 mL, 186 mmol) were added to a mixture of commercially available tert-butyl 4-hydroxy-1-piperidine carboxylate (15 g, 74.5 mmol) and tetrahydrofuran (200 mL) at 0° C., and the mixture was stirred for 30 minutes. Water and ethyl acetate were added to the reaction mixture for partition. The organic layer was dried and filtered by conventional methods. The solvent was evaporated, and the residue was collected by filteration and washed with n-heptane to obtain the title compound (19.8 g, 95%).

Workup

  1. customfor partition
  2. customThe organic layer was dried
  3. filtrationfiltered by conventional methods
  4. customThe solvent was evaporated
  5. customthe residue was collected by filteration
  6. washwashed with n-heptane

Sources & evidence

ORD record
ord-95e8791973f7489abfce5fb28080d16a
Source dataset
uspto-grants-2015_01
Patent number
US08933099B2

Reaction notes

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