Benzyloxyamine hydrochloride → HCID 53866658, compound

HRID 1886384Notes

Reaction equation

HRID 1886384 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]([CH:7]2[CH2:11][CH2:10][CH2:9][C:8]2=O)[CH:2]=1.Cl.[CH2:14]([O:21][NH2:22])[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1>N1C=CC=CC=1>[CH2:14]([O:21][N:22]=[C:8]1[CH2:9][CH2:10][CH2:11][CH:7]1[C:3]1[CH:2]=[N:1][CH:6]=[CH:5][CH:4]=1)[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1

Participants

4

Reactant 2

HCID 102312Benzyloxyamine hydrochlorideHCID 19876091HCID 19876091, compound

Product 1

HCID 53866658HCID 53866658, compound

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Conditions

Temperature
60 °C

Procedure

A mixture of (±)-2-(3-pyridyl)cyclopentanone (2.0 g) and benzyloxyamine hydrochloride (1.98 g) in anhydrous pyridine was stirred at 60° C. for 4.5 hours. The pyridine was removed in vacuo (40° C., 0.2 mmHg), the residue was dissolved in chloroform (75 ml), washed with water (4×75 ml), dried over magnesium sulphate and evaporated. The residual oil was purified by flash chromatography on silica, eluting with chloroform/methanol (100/1) to give (±)-2-benzyloxyimino -1-(3-pyridyl)cyclopentane (mixture of syn and anti isomers, 1:3), a pale yellow oil (2.91 g).

Workup

  1. customThe pyridine was removed in vacuo (40° C., 0.2 mmHg)
  2. dissolutionthe residue was dissolved in chloroform (75 ml)
  3. washwashed with water (4×75 ml)
  4. dry with materialdried over magnesium sulphate
  5. customevaporated
  6. customThe residual oil was purified by flash chromatography on silica
  7. washeluting with chloroform/methanol (100/1)

Sources & evidence

ORD record
ord-3366e50a53e54208abebb8b0de48c0a3
Source dataset
uspto-grants-1992_09
Patent number
US05151436

Reaction notes

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