Hydroxyamine hydrochloride → HCID 15295468, compound

HRID 2210550Notes

Reaction equation

HRID 2210550 reaction equation
C([O:3][C:4](=O)[C:5]([N:7]1[CH2:12][CH2:11][CH:10]([C:13]2[CH:18]=[CH:17][C:16]([O:19][CH3:20])=[C:15]([O:21][CH:22]3[CH2:26][CH2:25][CH2:24][CH2:23]3)[CH:14]=2)[CH2:9][CH2:8]1)=[O:6])C.Cl.[NH2:29][OH:30].[OH-].[K+].CO>CO>[CH:22]1([O:21][C:15]2[CH:14]=[C:13]([CH:10]3[CH2:11][CH2:12][N:7]([C:5](=[O:6])[C:4]([NH:29][OH:30])=[O:3])[CH2:8][CH2:9]3)[CH:18]=[CH:17][C:16]=2[O:19][CH3:20])[CH2:26][CH2:25][CH2:24][CH2:23]1

Participants

5

Reactant 3

HCID 443297Hydroxyamine hydrochlorideHCID 15295464HCID 15295464, compoundHCID 23689386Potassium hydroxide methanol

Product 1

HCID 15295468HCID 15295468, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a stirred solution of 2-[4-(3-cyclopentyloxy-4-methoxyphenyl)piperidin-1-yl]-2-oxo-acetic acid ethyl ester (5.3 mmol, 2.0 g) in methanol (55 mL) was added hydroxylamine hydrochloride (21.2 mmol, 1.5 g) followed by potassium hydroxide/methanol solution (5M; 5.3 mL) dropwise at room temperature. A white solid precipitated out of solution as this reaction stirred overnight. The reaction mixture was diluted with H2O (250 mL), acidified with 1N HCl (60 mL) and extracted with EtOAc (2×500 mL). Each organic phase was washed with H2O (250 mL) and the combined organics were dried (Na2SO4) and concentrated in vacuo to give a tan solid. The residue was purified by flash chromatography (SiO2 : 1) 80% EtOAc/hexane, 2) EtOAc) to afford the title compound as a white solid, mp=123.5°-124° C. (2.5 mmol, 0.920 g, 48%).

Workup

  1. customA white solid precipitated out of solution as this reaction
  2. additionThe reaction mixture was diluted with H2O (250 mL)
  3. extractionextracted with EtOAc (2×500 mL)
  4. washEach organic phase was washed with H2O (250 mL)
  5. dry with materialthe combined organics were dried (Na2SO4)
  6. concentrationconcentrated in vacuo
  7. customto give a tan solid
  8. customThe residue was purified by flash chromatography (SiO2 : 1) 80% EtOAc/hexane, 2) EtOAc)

Sources & evidence

ORD record
ord-9566c64e170d4b6682f9f0d1b504c787
Source dataset
uspto-grants-1995_10
Patent number
US05459151

Reaction notes

Loading…