Water → HCID 69758881, compound

HRID 2303398Notes

Reaction equation

HRID 2303398 reaction equation
[CH2:1]([C@:8]1([OH:15])[CH2:13][CH2:12][NH:11][CH2:10][C@@H:9]1[OH:14])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH2:16]([O:23][C:24]1[CH:29]=[CH:28][C:27]([O:30][CH2:31][CH2:32]Cl)=[CH:26][CH:25]=1)[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1.C([O-])([O-])=O.[K+].[K+].O>CN(C=O)C>[CH2:1]([C@:8]1([OH:15])[CH2:13][CH2:12][N:11]([CH2:32][CH2:31][O:30][C:27]2[CH:28]=[CH:29][C:24]([O:23][CH2:16][C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)=[CH:25][CH:26]=2)[CH2:10][C@@H:9]1[OH:14])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 18461181HCID 18461181, compoundHCID 59904579HCID 59904579, compound

Product 1

HCID 69758881HCID 69758881, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
90 °C

Procedure

To a solution of 0.2 g (1.0 mmol) (3R,4R) and (3S,4S)-4-benzyl-3,4-dihydroxy-piperidine in 10 ml DMF were added 297 mg (1.0 mmol) 1-benzyloxy-4-(2-chloro-ethoxy)-benzene and 0.2 g (1.5 mmol) K2CO3 and the reaction mixture was heated to 90° C. for 16 hours. After the addition of water, the aqueous phase was extracted three times with ethyl acetate and the combined organic layers were washed with water, dried over MgSO4 and the solvent was removed under reduced pressure to give 551 mg (100%, ˜80% purity) (3R,4R) and (3S,4S)-4-benzyl-1-[2-(4-benzyloxy-phenoxy)-ethyl]-piperidine-3,4-diol as a solid.

Workup

  1. extractionthe aqueous phase was extracted three times with ethyl acetate
  2. washthe combined organic layers were washed with water
  3. dry with materialdried over MgSO4
  4. customthe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-837ee121103d4a50843eb48243daedfe
Source dataset
uspto-grants-2002_08
Patent number
US06432985B1

Reaction notes

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