Hydrochloric Acid → N-Boc-3-mesyloxypiperidine

HRID 468566Notes

Reaction equation

HRID 468566 reaction equation
[C:1]([N:8]1[CH2:13][CH2:12][CH2:11][CH:10]([OH:14])[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].Cl>C(Cl)Cl.CCCCCCC.O>[C:1]([N:8]1[CH2:13][CH2:12][CH2:11][CH:10]([O:14][S:23]([CH3:22])(=[O:25])=[O:24])[CH2:9]1)([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2]

Participants

8

Reactant 4

HCID 313Hydrochloric AcidHCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 5456991-Boc-3-hydroxypiperidine

Product 1

HCID 568122N-Boc-3-mesyloxypiperidineYield 83.4%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6344DichloromethaneSolvent2×HCID 8900HeptaneSolvent

Conditions

Temperature
2.5 °C

Procedure

To a solution of 216 g of N-BOC-3(R,S)-hydroxypiperidine in 5 l of CH2Cl2 222 ml of triethylamine are added at 0-5° C. 137 g of methanesulfonyl chloride in 300 ml of CH2Cl2 are added dropwise over a period of 45 min, maintaining the temperature at 0-5° C. After additional stirring for 70 minutes 2 l of deionised water are added and the pH is adjusted to 5.9 by addition of about 90 ml of 2 n HCl. The aqueous phase is separated and the organic phase is washed with water. The solution is evaporated to dryness and 270-280 g of an oily residue are obtained. After treating with 1 l of n-heptane crystallization occurs. Crystals are isolated and dried in vacuo. 250 g of N-BOC-3(R,S)-methylsulfonyloxy-piperidine are obtained.

Workup

  1. additionare added
  2. customThe aqueous phase is separated
  3. washthe organic phase is washed with water
  4. customThe solution is evaporated to dryness and 270-280 g of an oily residue
  5. customare obtained
  6. customCrystals are isolated
  7. customdried in vacuo

Sources & evidence

ORD record
ord-6c131f9de07f440991663ec1e7900139
Source dataset
uspto-grants-2014_01
Patent number
US08624033B2

Reaction notes

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