Water → cis-l-Tert-butoxycarbonyl-3-hydroxy-4-methanesulfonyloxymethylpiperidine

HRID 344290Notes

Reaction equation

HRID 344290 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([CH2:14][OH:15])[CH:10]([OH:16])[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].C(N(CC)CC)C.[CH3:24][S:25](Cl)(=[O:27])=[O:26].O>ClCCl>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][C@H:11]([CH2:14][O:15][S:25]([CH3:24])(=[O:27])=[O:26])[C@H:10]([OH:16])[CH2:9]1)=[O:7])([CH3:4])([CH3:2])[CH3:3].[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][C@@H:11]([CH2:14][O:15][S:25]([CH3:24])(=[O:27])=[O:26])[C@H:10]([OH:16])[CH2:9]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

7

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 154810601,1-Dimethylethyl 3-hydroxy-4-(hydroxymethyl)-1-piperidinecarboxylate

Product 2

HCID 86753635cis-l-Tert-butoxycarbonyl-3-hydroxy-4-methanesulfonyloxymethylpiperidineHCID 86753636trans-1-Tert-butoxycarbonyl-3-hydroxy-4-methanesulfonyloxymethylpiperidine

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 1-tert-butoxycarbonyl-3-hydroxy-4-hydroxymethylpiperidine (6.5 g) and triethylamine (5.87 ml) in dichloromethane (100 ml) was added dropwise methanesulfonyl chloride (3.54 g) under ice-cooling, and the resulting mixture was stirred at room temperature for 6 hr. Water was added to the reaction mixture and the mixture was extracted with chloroform. The organic layer was washed with brine and dried. The solvent was evaporated under reduced pressure and the residue was purified by silica gel column chromatography (chloroform:methanol=40:1) to give 4.44 g of cis-l-tert-butoxycarbonyl-3-hydroxy-4-methanesulfonyloxymethylpiperidine and 0.93 g of trans-1-tert-butoxycarbonyl-3-hydroxy-4-methanesulfonyloxymethylpiperidine.

Workup

  1. temperaturecooling
  2. extractionthe mixture was extracted with chloroform
  3. washThe organic layer was washed with brine
  4. customdried
  5. customThe solvent was evaporated under reduced pressure
  6. customthe residue was purified by silica gel column chromatography (chloroform:methanol=40:1)

Sources & evidence

ORD record
ord-cb436ae2cbc1490ba74c7a83af05b90a
Source dataset
uspto-grants-1999_01
Patent number
US05864039

Reaction notes

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