Pyridine → N-BOC-3(R)-methylsulfonyloxymethyl-piperidine

HRID 720029Notes

Reaction equation

HRID 720029 reaction equation
[C:1]([N:8]1[CH2:13][CH2:12][CH2:11][CH:10]([CH2:14][OH:15])[CH2:9]1)([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2].N1C=CC=CC=1.[CH3:22][S:23](Cl)(=[O:25])=[O:24]>C(Cl)Cl>[C:4]([O:3][C:1]([N:8]1[CH2:13][CH2:12][CH2:11][C@@H:10]([CH2:14][O:15][S:23]([CH3:22])(=[O:25])=[O:24])[CH2:9]1)=[O:2])([CH3:7])([CH3:6])[CH3:5]

Participants

5

Reactant 3

HCID 1049PyridineHCID 31297Methanesulfonyl chlorideHCID 2763851tert-Butyl 3-(hydroxymethyl)piperidine-1-carboxylate

Product 1

HCID 10108453N-BOC-3(R)-methylsulfonyloxymethyl-piperidine

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of N-BOC-3-piperidinemethanol (0.50 g, 0.002 mmole) in DCM (10 mL) was added dropwise pyridine (2.42 mL, 0.03 mmole) followed by the addition of methanesulfonyl chloride (0.774 mL, 0.01 mmole). The reaction mixture continued stirring at RT overnight. The reaction mixture was quenched with water. The aqueous layer was extracted with EtOAc (3×5 mL). Combined organic layers were dried over Na2SO4 and concentrated to yield a crude oil, 68, which was used in the next step without further purification. LRMS: 193 (M+-BOC group).

Workup

  1. customThe reaction mixture was quenched with water
  2. extractionThe aqueous layer was extracted with EtOAc (3×5 mL)
  3. dry with materialCombined organic layers were dried over Na2SO4
  4. concentrationconcentrated
  5. customto yield a crude oil, 68, which
  6. customwas used in the next step without further purification

Sources & evidence

ORD record
ord-cec5e9591b3749c19449595e86e364ad
Source dataset
uspto-grants-2006_11
Patent number
US07132551B2

Reaction notes

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