HCID 22494777, compound → HCID 22494630, compound

HRID 1816710Notes

Reaction equation

HRID 1816710 reaction equation
Br[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][S:8][CH:9]1[CH2:14][CH2:13][N:12]([C:15]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16])[CH2:11][CH2:10]1.[CH3:22][OH:23].C[O-].[Na+]>CO>[CH3:22][O:23][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][S:8][CH:9]1[CH2:14][CH2:13][N:12]([C:15]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16])[CH2:11][CH2:10]1

Participants

4

Reactant 2

HCID 22494777HCID 22494777, compoundHCID 23694274Sodium methanolate methanol

Product 1

HCID 22494630HCID 22494630, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 4-(6-bromohexylthio)-N-t-butyloxycarbonylpiperidine (4.95 g) in methanol (20 ml) was added 28% sodium methoxide methanol solution (26.6 ml), and the mixture was stirred under reflux for 4 hours. After cooling, the reaction mixture was evaporated in vacuo. The resulting residue was chromatographed on silica gel (400 ml) eluting with a mixture of n-hexane and ethyl acetate (5:1 v/v). The fractions containing the object compound were collected and evaporated under reduced pressure to give 4-(6-methoxyhexylthio)-N-t-butyloxycarbonylpiperidine (3.32 g).

Workup

  1. temperatureunder reflux for 4 hours
  2. temperatureAfter cooling
  3. customthe reaction mixture was evaporated in vacuo
  4. customThe resulting residue was chromatographed on silica gel (400 ml)
  5. washeluting with a mixture of n-hexane and ethyl acetate (5:1 v/v)
  6. additionThe fractions containing the object compound
  7. customwere collected
  8. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-5eaf7f60e7ff4f8089ef2d3472298aea
Source dataset
uspto-grants-2005_04
Patent number
US06884868B1

Reaction notes

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