Sodium hydride → HCID 86751567, compound

HRID 2293308Notes

Reaction equation

Cl.[NH2:2][OH:3].[H-].[Na+].[CH2:6]([N:13]1[C:17](=[O:18])[CH:16]2[CH:19]([CH3:31])[N:20]([CH3:30])[CH:21]([C:22]3[CH:29]=[CH:28][C:25]([C:26]#[N:27])=[CH:24][CH:23]=3)[CH:15]2[C:14]1=[O:32])[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1>CN(C=O)C>[NH2:27][C:26](=[N:2][OH:3])[C:25]1[CH:28]=[CH:29][C:22]([CH:21]2[N:20]([CH3:30])[CH:19]([CH3:31])[CH:16]3[C:17](=[O:18])[N:13]([CH2:6][C:7]4[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=4)[C:14](=[O:32])[CH:15]23)=[CH:23][CH:24]=1

Participants

Conditions

Temperature: 0 °C

Procedure

841 mg (12.12 mmol) of hydroxylamine hydrochloride were suspended in 4 ml of DMF and cooled to 0° C. 303 mg (10.1 mmol) of 80% sodium hydride were added slowly. 365 mg (1.01 mmol) of (1RS,3SR,3aRS,6aSR)-4-(5-benzyl-2,3-dimethyl-4,6-dioxo-octahydro-pyrrolo[3,4-c]pyrrol-1-yl)-benzonitrile were dissolved in DMF and added to the reaction mixture. The cooling was thereafter no longer renewed. The mixture was stirred at room temperature for 5 days. Thereafter, it was filtered and the solvent was removed in a high vacuum. The mixture was purified chromatographically (RP18, gradient from water to methanol). 191 mg (48%) of (3aRS,4SR,6RS,6aSR)-4-[4-(amino-hydroxyimino-methyl)-phenyl]-2-benzyl-5,6-dimethyl-tetrahydro-pyrrolo[3,4-c]pyrrole-1,3-dione were isolated as a colourless powder. M.p.: 194°-196° C. ISP-MS: 393 ([M+H]+, 100); 303 (20); 219 (10).

Workup

additionadded to the reaction mixture
filtrationThereafter, it was filtered
customthe solvent was removed in a high vacuum
customThe mixture was purified chromatographically (RP18, gradient from water to methanol)

Sources & evidence

ORD record: ord-58507813d9444b8b863f92f47b0c0cc9
Source dataset: uspto-grants-1997_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05686459

Reaction notes

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