Water → HCID 86754766, compound

HRID 1602188Notes

Reaction equation

HRID 1602188 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][C@@H:11]([O:14][C:15]2[CH:20]=[CH:19][C:18]([O:21][C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=3)=[CH:17][CH:16]=2)[C@H:10]([OH:28])[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[H-].[Na+].[CH3:31][O:32][CH2:33][CH2:34]Br.O>CN(C=O)C>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][C@@H:11]([O:14][C:15]2[CH:16]=[CH:17][C:18]([O:21][C:22]3[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=3)=[CH:19][CH:20]=2)[C@H:10]([O:28][CH2:34][CH2:33][O:32][CH3:31])[CH2:9]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

6

Reactant 4

HCID 962WaterHCID 24758Sodium hydrideHCID 809722-Bromoethyl methyl etherHCID 86754767HCID 86754767, compound

Product 1

HCID 86754766HCID 86754766, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of (±)-trans-N-tert-butoxycarbonyl-3-hydroxy-4-(4-phenoxyphenoxy)-piperidine (1.47 g, 3.8 mmol) in dry DMF (30 ml) was added sodium hydride (300 mg 60% suspension in mineral oil, 4.2 mmol). After 1 h, 2-bromoethyl methyl ether (1.7 g, 7.6 mmol) was added. After 6 days water was added and the product was extracted with ethyl acetate (2×30 ml). After drying and evaporation the crude product was obtained as an oil.

Workup

  1. extractionthe product was extracted with ethyl acetate (2×30 ml)
  2. customAfter drying
  3. customevaporation the crude product
  4. customwas obtained as an oil

Sources & evidence

ORD record
ord-fe01928642c4420a91797f9590ad35ec
Source dataset
uspto-grants-1999_11
Patent number
US05981539

Reaction notes

Loading…