Hydroxyamine hydrochloride → HCID 57650158, compound

HRID 2063495Notes

Reaction equation

[Cl:1][C:2]1[CH:29]=[CH:28][C:5]([CH2:6][CH:7]([C:25](=O)[CH3:26])[C:8]([C@H:10]2[CH2:14][CH2:13][CH2:12][N:11]2[C:15]([O:17][CH2:18][C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)=[O:16])=[O:9])=[CH:4][CH:3]=1.Cl.[NH2:31]O>C(O)C.CCOC(C)=O>[Cl:1][C:2]1[CH:29]=[CH:28][C:5]([CH2:6][C:7]2[C:25]([CH3:26])=[N:31][O:9][C:8]=2[C@H:10]2[CH2:14][CH2:13][CH2:12][N:11]2[C:15]([O:17][CH2:18][C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)=[O:16])=[CH:4][CH:3]=1

Participants

Conditions

Temperature: 70 °C

Procedure

To a solution of (2R)-benzyl 2-(2-(4-chlorobenzyl)-3-oxobutanoyl)pyrrolidine-1-carboxylate (300 mg, 0.71 mmol) in ethanol (10 mL) was added hydroxylamine hydrochloride (490 mg, 7.1 mmol). The resulting solution was heated at 70° C. for 3 h and then diluted with EtOAc (30 mL). The organic layer was washed with saturated NaHCO3 solution (1×40 mL) and then brine (1×40 mL). The separated organic layer was then dried over Na2SO4 and concentrated in vacuo. Purification of the resulting residue by silica gel column chromatography (hexanes/ethyl acetate gradient, 10-100% EtOAc) afforded (R)-benzyl 2-(4-(4-chlorobenzyl)-3-methylisoxazol-5-yl)pyrrolidine-1-carboxylate (220 mg, 76%). LCMS: calculated: 410, found (MH+): 411.

Workup

washThe organic layer was washed with saturated NaHCO3 solution (1×40 mL)
dry with materialThe separated organic layer was then dried over Na2SO4
concentrationconcentrated in vacuo
customPurification of the resulting residue by silica gel column chromatography (hexanes/ethyl acetate gradient, 10-100% EtOAc)

Sources & evidence

ORD record: ord-4a20ba61984643da9841ea2cc3b1d389
Source dataset: uspto-grants-2012_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08288371B2

Reaction notes

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