Sodium hydride → HCID 178438338, compound

HRID 442743Notes

Reaction equation

Cl.[NH2:2][OH:3].[H-].[Na+].[O:6]1[C:10]2[CH:11]=[CH:12][C:13]([CH2:15][N:16]3[CH:20]([CH:21]([CH3:23])[CH3:22])[CH:19]4[C:24]([CH3:37])([CH3:36])[N:25]([CH3:35])[CH:26]([C:27]5[CH:34]=[CH:33][C:30]([C:31]#[N:32])=[CH:29][CH:28]=5)[CH:18]4[C:17]3=[O:38])=[CH:14][C:9]=2[O:8][CH2:7]1>CN(C=O)C>[O:6]1[C:10]2[CH:11]=[CH:12][C:13]([CH2:15][N:16]3[CH:20]([CH:21]([CH3:23])[CH3:22])[CH:19]4[C:24]([CH3:36])([CH3:37])[N:25]([CH3:35])[CH:26]([C:27]5[CH:28]=[CH:29][C:30]([C:31](=[NH:32])[NH:2][OH:3])=[CH:33][CH:34]=5)[CH:18]4[C:17]3=[O:38])=[CH:14][C:9]=2[O:8][CH2:7]1

Participants

Conditions

Temperature: 0 °C

Procedure

841 mg (12.12 mmol) of hydroxylamine hydrochloride are suspended in 4 ml of DMF and cooled to 0° C. 303 mg (10.1 mmol) of 80% sodium hydride are added slowly. 500 mg (1.13 mmol) of (1RS,3aSR,4RS,6aSR)-4-(5-benzo[1,3]dioxol-5-ylmethyl-4-isopropyl-2,3,3-trimethyl-6-oxo-octahydro-pyrrolo[3,4-c]pyrrol-1-yl)-benzonitrile are dissolved in DMF and added to the reaction mixture. The cooling is thereafter no longer applied. The mixture is stirred at room temperature for 5 days. Thereafter, it is filtered and the solvent is removed in a high vacuum. The mixture is purified by chromatography (RP18, gradient from water to methanol). (1RS,3aSR,4RS,6aSR)-4-(5-Benzo[1,3]dioxol-5-ylmethyl-4-isopropyl-2,3,3-trimethyl-6-oxo-octahydro-pyrrolo[3,4-c]pyrrol-1-yl)-N-hydroxy-benzimidamide is isolated in 66% yield. Colourless solid. ISP-MS: 479.4 ([M+H]+, 100).

Workup

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

Sources & evidence

ORD record: ord-895d9cba44934338aa35f5d7829aa252
Source dataset: uspto-grants-1999_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05891900

Reaction notes

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