Ethyl Acetate → HCID 70245767, compound

HRID 1976233Notes

Reaction equation

[Si:1]([O:8][C@H:9]1[CH2:18][N:17]2[C@H:11]([C:12](=O)[NH:13][C:14]3[CH:23]=[CH:22][CH:21]=[CH:20][C:15]=3[C:16]2=[O:19])[CH2:10]1)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].[H-].[Al+3].[Li+].[H-].[H-].[H-].C(OCC)(=O)C.[Cl-].[NH4+]>O1CCCC1>[Si:1]([O:8][C@H:9]1[CH2:18][N:17]2[C@H:11]([CH2:12][NH:13][C:14]3[CH:23]=[CH:22][CH:21]=[CH:20][C:15]=3[C:16]2=[O:19])[CH2:10]1)([C:4]([CH3:7])([CH3:5])[CH3:6])([CH3:3])[CH3:2]

Participants

Conditions

Temperature: 50 °C

Procedure

A solution of (2R,11aS)-2-(tert-butyldimethylsilyloxy)-1,2,3,10,11,11a-hexahydro-5H-pyrrolo[2,1-c][1,4]benzodiazepin-5,11-dione (34.6 g) in tetrahydrofuran (100 ml) was dropwise added to a suspension of lithium aluminum hydride (4.2 g) in tetrahydrofuran (200 ml) at 0° C. over 15 minutes in a nitrogen gas atmosphere, followed by stirring at room temperature for one hour and at 50° C. for one hour. After ice-cooling the reaction solution, 30 ml of ethyl acetate and 8 ml of a saturated aqueous ammonium chloride solution were added to the reaction solution, the mixture was stirred for 30 minutes and the precipitates separated out were filtered off. The filtrate was dried, concentrated under reduced pressure and the resulting residue was recrystallized from ethyl acetate to give 18.4 g (yield 55.3%) of the title compound.

Workup

additionwere added to the reaction solution
stirringthe mixture was stirred for 30 minutes
customthe precipitates separated out
filtrationwere filtered off
customThe filtrate was dried
concentrationconcentrated under reduced pressure
customthe resulting residue was recrystallized from ethyl acetate

Sources & evidence

ORD record: ord-6c6af8879ee04d2f9ffbd406070a22ac
Source dataset: uspto-grants-2001_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06225306B1

Reaction notes

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