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

HRID 85110Notes

Reaction equation

HRID 85110 reaction equation
[C:1]([N:8]1[CH2:13][CH2:12][CH:11]([OH:14])[CH2:10][CH2:9]1)([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2].CCN(CC)CC.[CH3:22][S:23](Cl)(=[O:25])=[O:24]>C(Cl)Cl>[CH3:22][S:23]([O:14][CH:11]1[CH2:12][CH2:13][N:8]([C:1]([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2])[CH2:9][CH2:10]1)(=[O:25])=[O:24]

Participants

5

Reactant 3

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

Product 1

HCID 41848691-(tert-Butoxycarbonyl)-4-(methanesulfonyloxy)piperidine

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent3×

Procedure

To a solution of N-Boc-4-hydroxypiperidine (22; 25 g, 124 mmol) and Et3N (20.7 mL) in CH2Cl2 (100 mL) was added a solution of methanesulfonyl chloride 23 in CH2Cl2 (20 mL) dropwise in an ice-water bath. The mixture was stirred at room temperature for 18 h. It was then diluted with 100 mL of CH2Cl2 and washed successively with saturated aqueous Na2CO3 (50 mL) and brine (50 mL). The organic layer was dried (Na2SO4) and concentrated under reduced pressure to afford tert-butyl 4-(methylsulfonyloxy)piperidine-1-carboxylate 24 (45 g, crude yield: >100%). This material was then used in the next step without further purification.

Workup

  1. washwashed successively with saturated aqueous Na2CO3 (50 mL) and brine (50 mL)
  2. dry with materialThe organic layer was dried (Na2SO4)
  3. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-e3702643af6842cea5740252d3fbd714
Source dataset
uspto-grants-2014_09
Patent number
US08846947B2

Reaction notes

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