Triethylamine → N-Boc-3-mesyloxypiperidine

HRID 1643462Notes

Reaction equation

HRID 1643462 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].C(=O)(O)[O-].[Na+]>O1CCCC1.C(OCC)(=O)C>[CH3:22][S:23]([O:14][CH:10]1[CH2:11][CH2:12][CH2:13][N:8]([C:1]([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2])[CH2:9]1)(=[O:25])=[O:24]

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 516892Sodium BicarbonateHCID 5456991-Boc-3-hydroxypiperidine

Product 1

HCID 568122N-Boc-3-mesyloxypiperidine

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

1-Boc-3-hydroxypiperidine (0.5 g, 2.49 mmol) was dissolved in tetrahydrofuran (5 ml), triethylamine (0.75 g, 7.46 mmol) was added and the mixture was cooled. Methanesulfonic acid chloride (0.23 ml, 3 mmol) was added, the mixture was stirred in an ice bath for 10 min, saturated sodium bicarbonate solution (10 ml) was then added, as well as ethyl acetate (10 ml). Phase separation, the aqueous phase was extracted with ethyl acetate (2×20 ml) and the combined organic phases were washed with saturated sodium chloride solution (20 ml), dried over sodium sulfate and concentrated in vacuo. Yield: 0.54 g (77%)

Workup

  1. temperaturethe mixture was cooled
  2. customPhase separation
  3. extractionthe aqueous phase was extracted with ethyl acetate (2×20 ml)
  4. washthe combined organic phases were washed with saturated sodium chloride solution (20 ml)
  5. dry with materialdried over sodium sulfate
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-1a4ff3d83ac140b98f8b7d68a67873d3
Source dataset
uspto-grants-2012_02
Patent number
US08119805B2

Reaction notes

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