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

HRID 1852716Notes

Reaction equation

HRID 1852716 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].C(N(CC)CC)C.[CH3:22][S:23](Cl)(=[O:25])=[O:24].O>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

6

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 643502Tert-butyl 4-hydroxypiperidine-1-carboxylate

Product 1

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

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To N-Boc-4-hydroxypiperidine (2200 g, 10.95 mol) in anhydrous DCM (8 L) was added triethylamine (2284 mL, 16.42 mol) in one portion at 0° C., then MsCl (1316 g, 11.49 mol) was added drop wise into the mixture at 0° C. The mixture was stirred at room temperature for 2 h. Water (2 L) was added to the mixture and the organic phase was separated, and then the organic phase was washed with 1 M hydrochloride solution (4 L), saturated NaHCO3 solution (4 L), brine (1 L), and dried over anhydrous Na2SO4. The organic layer was concentrated to afford tert-butyl 4-[(methylsulfonyl)oxy]piperidine-1-carboxylate, which was used for the next step without further purification.

Workup

  1. customthe organic phase was separated
  2. washthe organic phase was washed with 1 M hydrochloride solution (4 L), saturated NaHCO3 solution (4 L), brine (1 L)
  3. dry with materialdried over anhydrous Na2SO4
  4. concentrationThe organic layer was concentrated

Sources & evidence

ORD record
ord-2d127eaeda2f4d669e2bdea00a276099
Source dataset
uspto-grants-2015_02
Patent number
US08962611B2

Reaction notes

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