Methanesulfonyl chloride → HCID 11151879, compound

HRID 1971296Notes

Reaction equation

HRID 1971296 reaction equation
[CH3:1][S:2](Cl)(=[O:4])=[O:3].[OH:6][C@H:7]1[CH2:12][CH2:11][N:10]([C:13]([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14])[C@@H:9]([C:20]([O:22][CH3:23])=[O:21])[CH2:8]1>CN(C1C=CN=CC=1)C.N1C=CC=CC=1>[CH3:1][S:2]([O:6][C@H:7]1[CH2:12][CH2:11][N:10]([C:13]([O:15][C:16]([CH3:17])([CH3:18])[CH3:19])=[O:14])[C@@H:9]([C:20]([O:22][CH3:23])=[O:21])[CH2:8]1)(=[O:4])=[O:3]

Participants

5

Reactant 2

HCID 31297Methanesulfonyl chlorideHCID 2734504(2R,4S)-N-Boc-4-Hydroxypiperidine-2-Carboxylic Acid Methyl Ester

Product 1

HCID 11151879HCID 11151879, compoundYield 98%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 1049PyridineSolvent

Procedure

MsCl (6.61 mL, 85 mmol) was added dropwise at 0° C. to a solution of (2R,4S)-1-tert-butyl 2-methyl 4-hydroxypiperidine-1,2-dicarboxylate (21 g, 81 mmol) and DMAP (100 mg, 0.81 mmol) in pyridine (50 mL). The mixture was stirred at room temperature for 5 hours and then was concentrated under reduced pressure to remove most solvent. Brine (200 mL) was added and extracted with ethyl acetate (2×200 mL). The organic layer was dried over MgSO4, filtered and concentrated under reduced pressure to give title compound 26.7 g (98%) as colorless oil. LC-MS: 338.1 (t=1.9 min).

Workup

  1. concentrationwas concentrated under reduced pressure
  2. customto remove most solvent
  3. additionBrine (200 mL) was added
  4. extractionextracted with ethyl acetate (2×200 mL)
  5. dry with materialThe organic layer was dried over MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-aae090b54b3c481bb246fa4fd4bb5e91
Source dataset
uspto-grants-2013_04
Patent number
US08431597B2

Reaction notes

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