HCID 22492926, compound → HCID 22492895, compound

HRID 1816694Notes

Reaction equation

HRID 1816694 reaction equation
Br[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][O:7][CH:8]1[CH2:13][CH2:12][N:11]([C:14]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15])[CH2:10][CH2:9]1.[CH3:21][OH:22].C[O-].[Na+]>CO>[CH3:21][O:22][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][O:7][CH:8]1[CH2:13][CH2:12][N:11]([C:14]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15])[CH2:10][CH2:9]1

Participants

4

Reactant 2

HCID 22492926HCID 22492926, compoundHCID 23694274Sodium methanolate methanol

Product 1

HCID 22492895HCID 22492895, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 4-(5-bromopentyloxy)-1-N-t-butyloxycarbonylpiperidine (2.44 g) in methanol (13 ml) was added 28% sodium methoxide methanol solution (14.2 ml), and the mixture was stirred under reflux for 4 hours. The reaction mixture was evaporated in vacuo. The resulting residue was chromatographed on silica gel (250 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-(5-methoxypentyloxy)-1-N-t-butyloxycarbonylpiperidine (1.97 g).

Workup

  1. temperatureunder reflux for 4 hours
  2. customThe reaction mixture was evaporated in vacuo
  3. customThe resulting residue was chromatographed on silica gel (250 ml)
  4. washeluting with a mixture of n-hexane and ethyl acetate (5:1 v/v)
  5. additionThe fractions containing the object compound
  6. customwere collected
  7. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-f170ae24fe89475985bee857ff8db7e1
Source dataset
uspto-grants-2005_04
Patent number
US06884868B1

Reaction notes

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