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

HRID 1373361Notes

Reaction equation

HRID 1373361 reaction equation
C(N(CC)CC)C.[OH:8][CH:9]1[CH2:14][CH2:13][N:12]([C:15]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16])[CH2:11][CH2:10]1.[CH3:22][S:23](Cl)(=[O:25])=[O:24]>ClCCl.O>[CH3:22][S:23]([O:8][CH:9]1[CH2:10][CH2:11][N:12]([C:15]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16])[CH2:13][CH2:14]1)(=[O:25])=[O:24]

Participants

6

Reactant 3

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

Product 1

HCID 41848691-(tert-Butoxycarbonyl)-4-(methanesulfonyloxy)piperidineYield 89%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent2×

Procedure

Triethylamine (1.4 ml, 10 mmol) was added to a stirred solution of tert-butyl 4-hydroxy-1-piperidine-carboxylate (2.0 g, 9.94 mmol) in dichloromethane (40 ml) at −17° C. under nitrogen. Methanesulfonyl chloride (0.85 ml, 11 mmol) was added dropwise and the mixture allowed to warm up to room temperature overnight. The reaction mixture was diluted with dichloromethane (50 ml) and water (100 ml) was added. The organic layer was separated and the aqueous phase was re-extracted with dichloromethane (2×50 ml). The combined organic layers were dried (MgSO4) and evaporated under reduced pressure. The residue was purified by flash chromatography eluting with 50% ethyl acetate in iso hexanes to give tert-butyl 4-methanesulfonyloxy-piperidine-1-carboxylate as a colourless oil (2.47 g, 89%),

Workup

  1. additionwas added
  2. customThe organic layer was separated
  3. extractionthe aqueous phase was re-extracted with dichloromethane (2×50 ml)
  4. dry with materialThe combined organic layers were dried (MgSO4)
  5. customevaporated under reduced pressure
  6. customThe residue was purified by flash chromatography
  7. washeluting with 50% ethyl acetate in iso hexanes

Sources & evidence

ORD record
ord-b3ba980eb5fe41189a7954a69545cb5a
Source dataset
uspto-grants-2007_01
Patent number
US07161006B2

Reaction notes

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