Methanesulfonyl chloride → Benzyl 4-fluoro-4-{[(methylsulfonyl)oxy]methyl}piperidine-1-carboxylate

HRID 854330Notes

Reaction equation

HRID 854330 reaction equation
[F:1][C:2]1([CH2:18][OH:19])[CH2:7][CH2:6][N:5]([C:8]([O:10][CH2:11][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)=[O:9])[CH2:4][CH2:3]1.[CH3:20][S:21](Cl)(=[O:23])=[O:22]>C(Cl)Cl>[F:1][C:2]1([CH2:18][O:19][S:21]([CH3:20])(=[O:23])=[O:22])[CH2:3][CH2:4][N:5]([C:8]([O:10][CH2:11][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)=[O:9])[CH2:6][CH2:7]1

Participants

4

Reactant 2

HCID 31297Methanesulfonyl chlorideHCID 22135584Benzyl 4-fluoro-4-(hydroxymethyl)piperidine-1-carboxylate

Product 1

HCID 22135556Benzyl 4-fluoro-4-{[(methylsulfonyl)oxy]methyl}piperidine-1-carboxylate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of benzyl 4-fluoro-4-(hydroxymethyl)piperidine-1-carboxylate (1.0 g, 3.7 mmol) in CH2Cl2 (10 mL) at RT was added MsCl (0.29 mL, 3.7 mmol) and TEA (1.04 mL, 7.5 mmol). The reaction mixture was stirred at RT for 5 min, and partitioned between EtOAc and H2O. The organic layer was dried over Na2SO4, filtered, concentrated and purified on silica gel (10:1 to 1:2 hexanes:EtOAc) to give benzyl 4-fluoro-4-{[(methylsulfonyl)oxy]methyl}piperidine-1-carboxylate.

Workup

  1. custompartitioned between EtOAc and H2O
  2. dry with materialThe organic layer was dried over Na2SO4
  3. filtrationfiltered
  4. concentrationconcentrated
  5. custompurified on silica gel (10:1 to 1:2 hexanes:EtOAc)

Sources & evidence

ORD record
ord-f81ca437702d40e4bf7acb49c8587468
Source dataset
uspto-grants-2007_08
Patent number
US07259157B2

Reaction notes

Loading…