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

HRID 1813989Notes

Reaction equation

HRID 1813989 reaction equation
[OH:1][CH:2]1[CH2:7][CH2:6][N:5]([C:8]([O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[O:9])[CH2:4][CH2:3]1.C(N(CC)CC)C.[CH3:22][S:23](Cl)(=[O:25])=[O:24].O>C(Cl)Cl>[CH3:22][S:23]([O:1][CH:2]1[CH2:3][CH2:4][N:5]([C:8]([O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[O:9])[CH2:6][CH2:7]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 6344DichloromethaneSolvent2×

Conditions

Temperature
0 °C

Procedure

tert-Butyl 4-hydroxypiperidine-1-carboxylate 5-1 (21.650 g, 107.57 mmol) was dissolved in 200 mL CH2Cl2. N,N,N-Triethylamine (17.991 mL, 129.08 mmol) was added and the solution was cooled to 0° C. A solution of methanesulfonyl chloride (9.991 mL, 129.08 mmol) in 50 mL CH2Cl2 was then added dropwise. The solution was allowed to warm to room temperature. After 3.5 hours, 100 mL H2O was added and the solution was stirred for 0.5 hour. The organic layer was separated, washed with 0.5N HCl and saturated NaHCO3 (aq), dried (Na2SO4), filtered, and concentrated to afford tert-butyl 4-[(methylsulfonyl)oxy]piperidine-1-carboxylate 5-2 as an off white solid. 1H NMR (CDCl3) δ 4.89 (m, 1H), 3.75-3.67 (m, 2H), 3.35-3.26 (m, 2H), 3.04 (s, 3H), 2.05-1.94 (m, 2H), 1.87-1.79 (m, 2H), 1.46 (s, 9H).

Workup

  1. temperatureto warm to room temperature
  2. customThe organic layer was separated
  3. washwashed with 0.5N HCl and saturated NaHCO3 (aq)
  4. dry with materialdried (Na2SO4)
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-361191af8299437ebf118bf8d068b248
Source dataset
uspto-grants-2005_04
Patent number
US06875767B2

Reaction notes

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