Hydroxylamine → HCID 22137576, compound

HRID 865718Notes

Reaction equation

HRID 865718 reaction equation
C(OC([N:11]1[CH2:16][CH2:15][CH:14](N2CCOC2=O)[CH2:13][CH2:12]1)=O)C1C=CC=CC=1.NO.[C:25](N1C=CN=C1)([N:27]1[CH:31]=[CH:30]N=C1)=[O:26]>C(Cl)(Cl)Cl.ClCCl>[O:26]1[CH2:30][CH2:31][N:27]([N:11]2[CH2:12][CH2:13][CH2:14][CH2:15][CH2:16]2)[CH2:25]1

Participants

6

Reactant 3

HCID 787HydroxylamineHCID 682631,1'-CarbonyldiimidazoleHCID 22137525HCID 22137525, compound

Product 1

HCID 22137576HCID 22137576, compound

Reagents, catalysts & solvents 2

HCID 6212ChloroformSolventHCID 6344DichloromethaneSolvent

Procedure

1-Benzyloxycarbonyl-4-(2-oxo-1,3-oxazolidin-3-yl)piperidine. A solution of the amino alcohol (1.7 g) and 1,1'-carbonyldiimidazole (2.4 g) in chloroform (30 mL) was heated at reflux for 6 hours. The reaction mixture was diluted with dichloromethane and washed with 1N sodium hydroxide and water. The separated organic phase was dried and evaporated to give the oxazolidin-3-yl piperidine as a viscous oil (1.9 g); NMR: 7.35 (m,5), 5.13 (s,2), 4.34 (m,4), 3.89 (m,1), 3.49 (m,2), 2.86 (m,2), 1.78 (m,2), 1.58 (m,2); MS: m/z=305(M+1).

Workup

  1. temperatureat reflux for 6 hours
  2. washwashed with 1N sodium hydroxide and water
  3. customThe separated organic phase was dried
  4. customevaporated

Sources & evidence

ORD record
ord-500f89d9ecef468ab540e65b7e5bb288
Source dataset
uspto-grants-1996_10
Patent number
US05567700

Reaction notes

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