Sodium hydride → (3aRS,4RS,6aSR)-4-[4-(amino-hydroxyimino-methyl)-benzyl]-2-benzyl-5,6,6-trimethyl-tetrahydro-pyrrolo[3,4-c]pyrrole-1,3-dione

HRID 2293302Notes

Reaction equation

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

Participants

Conditions

Temperature: 0 °C

Procedure

2.19 g (31.56 mmol) of hydroxylamine hydrochloride were suspended in 8 ml of DMF and cooled to 0° C. 0.79 g (26.3 mmol) of 80% sodium hydride was added slowly. 1.02 g (2.63 mmol) of (1RS, 3aSR,6aRS)-4-(5-benzyl-2,3,3-trimethyl-4,6-dioxo-octahydro-pyrrolo[3,4-c]pyrrol-1-ylmethyl)-benzonitrile were dissolved in DMF and added to the reaction mixture. The cooling was then no longer applied. The mixture was stirred at room temperature for 2 days. Thereafter, it was filtered and the DMF was removed in a high vacuum. The mixture was purified chromatographically (RP18, gradient from water to methanol). 1.08 g (97%) of (3aRS,4RS,6aSR)-4-[4-(amino-hydroxyimino-methyl)-benzyl]-2-benzyl-5,6,6-trimethyl-tetrahydro-pyrrolo[3,4-c]pyrrole-1,3-dione were isolated as a colourless powder. M.p.: 189°-192° C. ISP-MS: 421.5 ([M+H]+, 100).

Workup

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

Sources & evidence

ORD record: ord-ba980332df26429d9a45ea4cb65ea0be
Source dataset: uspto-grants-1997_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05686459

Reaction notes

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