Diisopropylamine → HCID 20464725, compound

HRID 325435Notes

Reaction equation

C(NC(C)C)(C)C.[Li+].CCC[CH2-].[Cl:13][C:14]1[CH:30]=[CH:29][C:17]2[C:18](=[O:28])[C:19]3[N:20]([CH3:27])[C:21]([CH3:26])=[CH:22][C:23]=3[CH2:24][O:25][C:16]=2[CH:15]=1.C[O:32][C:33](=O)[O:34]C>O1CCCC1>[Cl:13][C:14]1[CH:30]=[CH:29][C:17]2[C:18](=[O:28])[C:19]3[N:20]([CH3:27])[C:21]([CH2:26][C:33]([OH:34])=[O:32])=[CH:22][C:23]=3[CH2:24][O:25][C:16]=2[CH:15]=1

Participants

Conditions

Temperature: -78 °C

Procedure

To a stirred, cooled (0° C.) solution of diisopropylamine (12.5 g, 0.124 m) in dry tetrahydrofuran (40 ml) under a nitrogen atmosphere is added N-butyllithium (0.124 m) and the solution stirred for 10 minutes followed by cooling to -78° C. A mixture of 7-chloro-1,2-dimethyl-4,10-dihydro-10-oxo-1H[1]benzoxepino[4,3-b]pyrrole (31.3 g, 0.12 m), dimethylcarbonate (11.7 g, 0.13 m) and tetrahydrofuran (50 ml) is then added dropwise over 10 min. The bath is then removed and the mixture allowed to warm to room temperature and is stirred for four hours. Water (50 ml) is added and the reaction mixture is further stirred overnight. Aqueous sodium hydroxide is then added and the mixture is filtered. The filtrate is acidified to yield 7-chloro-4,10-dihydro-1-methyl-10-oxo-1H[1]benzoxepino[4,3-b]pyrrole-2-acetic acid.

Workup

additionis then added dropwise over 10 min
customThe bath is then removed
temperatureto warm to room temperature
stirringis stirred for four hours
additionWater (50 ml) is added
stirringthe reaction mixture is further stirred overnight
additionAqueous sodium hydroxide is then added
filtrationthe mixture is filtered

Sources & evidence

ORD record: ord-e04d90c99ce94259a7cc2048b61def08
Source dataset: uspto-grants-1984_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04440779

Reaction notes

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