Hydroxyamine hydrochloride → HCID 57650417, compound

HRID 2063488Notes

Reaction equation

HRID 2063488 reaction equation
[Cl:1][C:2]1[CH:27]=[CH:26][C:5]([CH2:6][C:7](=[CH:22][N:23](C)C)[C:8]([C@H:10]2[CH2:14][CH2:13][CH2:12][N:11]2[C:15]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16])=[O:9])=[CH:4][CH:3]=1.Cl.NO>C(O)C>[Cl:1][C:2]1[CH:27]=[CH:26][C:5]([CH2:6][C:7]2[CH:22]=[N:23][O:9][C:8]=2[C@H:10]2[CH2:14][CH2:13][CH2:12][N:11]2[C:15]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16])=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 443297Hydroxyamine hydrochlorideHCID 68811060HCID 68811060, compound

Product 1

HCID 57650417HCID 57650417, compoundYield 75.3%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
70 °C

Procedure

To a solution of (R)-tert-butyl 2-(2-(4-chlorobenzyl)-3-(dimethylamino)acryloyl)pyrrolidine-1-carboxylate (580 mg, 1.5 mmol) in ethanol (10 mL) was added hydroxylamine hydrochloride (210 mg, 3 mmol). The resulting solution was heated at 70° C. for 2 h and then concentrated in vacuo. Purification of the resulting residue by silica gel column chromatography (hexanes/ethyl acetate gradient, 10-100% EtOAc) afforded (R)-tert-butyl 2-(4-(4-chlorobenzyl)isoxazol-5-yl)pyrrolidine-1-carboxylate (410 mg, 75%). LCMS: calculated: 365, found (M-tBuH+): 307

Workup

  1. concentrationconcentrated in vacuo
  2. customPurification of the resulting residue by silica gel column chromatography (hexanes/ethyl acetate gradient, 10-100% EtOAc)

Sources & evidence

ORD record
ord-27986bd35acb43249c613fdae6e5e851
Source dataset
uspto-grants-2012_10
Patent number
US08288371B2

Reaction notes

Loading…