Methanesulfonyl chloride → HCID 15550579, compound

HRID 2268944Notes

Reaction equation

HRID 2268944 reaction equation
[CH2:1]([O:8][C:9]([N:11]1[CH2:16][CH2:15][CH2:14][CH:13]([CH2:17][OH:18])[CH2:12]1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(N(C(C)C)CC)(C)C.[CH3:28][S:29](Cl)(=[O:31])=[O:30]>C(Cl)Cl>[CH2:1]([O:8][C:9]([N:11]1[CH2:16][CH2:15][CH2:14][CH:13]([CH2:17][O:18][S:29]([CH3:28])(=[O:31])=[O:30])[CH2:12]1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 31297Methanesulfonyl chlorideHCID 81531DiisopropylethylamineHCID 2776577Benzyl 3-(hydroxymethyl)piperidine-1-carboxylate

Product 1

HCID 15550579HCID 15550579, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of 1-benzyloxycarbonyl-3-hydroxymethyl-piperidine (1.29 g, 5.24 mmol, 1 eq) in CH2Cl2 (50 mL) at 0° C. was added diisopropylethylamine (2.7 mL, 15.72 mmol, 3 eq) followed by methanesulfonylchloride (0.61 mL, 7.86 mmol, 1.5 eq) via syringe. Let stir 10 minutes and removed the cooling bath. After 30 minutes the reaction was complete by thin layer chromatography analysis. Removed the CH2Cl2 under reduced pressure and used material crude in the next step.

Workup

  1. customremoved the cooling bath
  2. waitAfter 30 minutes the reaction was complete by thin layer chromatography analysis
  3. customRemoved the CH2Cl2 under reduced pressure

Sources & evidence

ORD record
ord-8c19dd44dbd249858fc11d39bfd2cbd1
Source dataset
uspto-grants-2001_12
Patent number
US06329380B1

Reaction notes

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