Triethylamine → N-Boc-3-mesyloxypiperidine

HRID 1584265Notes

Reaction equation

HRID 1584265 reaction equation
[CH3:1][S:2]([O:5]S(C)(=O)=O)(=[O:4])=[O:3].O[CH:11]1[CH2:16][CH2:15][CH2:14][N:13]([C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18])[CH2:12]1.C(N(CC)CC)C>C(Cl)Cl>[CH3:1][S:2]([O:5][CH:15]1[CH2:16][CH2:11][CH2:12][N:13]([C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18])[CH2:14]1)(=[O:4])=[O:3]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 81560Methanesulfonic anhydrideHCID 5456991-Boc-3-hydroxypiperidine

Product 1

HCID 568122N-Boc-3-mesyloxypiperidine

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Methanesulfonic anhydride (996 mg, 5.72 mmol) was added to a mixture of 3-hydroxy-N-t-butoxycarbonylpiperidine (959 mg, 4.76 mmol) and triethylamine (0.86 ml, 6.19 mmol) in methylene chloride (30 ml) at 0° C. After stirring for 1 h, the reaction mixture was washed with saturated NaHCO3 and dried (Na2SO4). Concentration gave the title compound. 1H NMR (CDCl3) d 1.46 (s, 9 H), 1.77-2.17 (m, 4 H), 3.05 (s, 3 H), 3.14-3.49 (m, 2 H), 3.62 (m, 2 H), 4.72 (br s, 1 H).

Workup

  1. washthe reaction mixture was washed with saturated NaHCO3
  2. dry with materialdried (Na2SO4)
  3. concentrationConcentration

Sources & evidence

ORD record
ord-44d77ccb06a34a5f9bbe92bdb8b306c8
Source dataset
uspto-grants-1999_08
Patent number
US05932606

Reaction notes

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