Water → HCID 57588246, compound

HRID 1868361Notes

Reaction equation

HRID 1868361 reaction equation
[H-].[Na+].[OH:3][C@H:4]1[C@H:9]([CH2:10][O:11][S:12]([C:15]2[CH:20]=[CH:19][C:18]([CH3:21])=[CH:17][CH:16]=2)(=[O:14])=[O:13])[CH2:8][CH2:7][N:6]([C:22]([O:24][C:25]([CH3:28])([CH3:27])[CH3:26])=[O:23])[CH2:5]1.[CH3:29]I.O>C1COCC1>[CH3:21][C:18]1[CH:19]=[CH:20][C:15]([S:12]([O:11][CH2:10][C@@H:9]2[CH2:8][CH2:7][N:6]([C:22]([O:24][C:25]([CH3:28])([CH3:27])[CH3:26])=[O:23])[CH2:5][C@H:4]2[O:3][CH3:29])(=[O:13])=[O:14])=[CH:16][CH:17]=1

Participants

6

Reactant 4

HCID 962WaterHCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 11383575rel-1,1-Dimethylethyl (3R,4R)-3-hydroxy-4-[[[(4-methylphenyl)sulfonyl]oxy]methyl]-1-piperidinecarboxylate

Product 1

HCID 57588246HCID 57588246, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Reaction under nitrogen atmosphere. Sodiumhydride (0.3 mol) was added to a solution of 1,1-dimethylethyl trans-3-hydroxy-4-[[[(4-methylphenyl)sulfonyl]oxy]methyl]-1-piperidinecarboxylate [described in WO-00/37461 as intermediate (1-c)] (0.27 mol) in THF (1300 ml). The mixture was stirred for 30 minutes. Methyliodide (0.54 mol) was added and the resulting reaction mixture was stirred for 90 minutes. A small amount of water was added. The solvent was evaporated and the residue was partitioned between water and DCM. The organic layer was separated, dried, filtered and the solvent was evaporated, yielding 1,1-dimethylethyl trans-4-[[[(4-methylphenyl)sulfonyl]oxy]-methyl]-3-methoxy-1-piperidinecarboxylate (intermediate 23).

Workup

  1. customReaction under nitrogen atmosphere
  2. customthe resulting reaction mixture
  3. stirringwas stirred for 90 minutes
  4. customThe solvent was evaporated
  5. customthe residue was partitioned between water and DCM
  6. customThe organic layer was separated
  7. customdried
  8. filtrationfiltered
  9. customthe solvent was evaporated

Sources & evidence

ORD record
ord-a3de3d3fdacb4d28ac2bb4658bd37dfa
Source dataset
uspto-grants-2009_12
Patent number
US07635706B2

Reaction notes

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