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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 1417628Generated: October 31, 2026

Sodium Bicarbonate → (6aR,7S,9aS,13aS)-5-benzyloxy-2,3,6,6a,7,8,9,9a,10,11,12,13-dodecahydro-6a,7,10,10-tetramethyl-11-(1-oxa-4-azacyclohex-4-yl)imino-3-oxo-1H-benzo[8,8a][1]benzopyrano[2,3-e]isoindole

https://huagongshe.com/reaction/1417628

Reaction equation

Participants

RoleNameHCIDCharge
ReactantSodium BicarbonateHCID 516892—
Reactant1,4-Dioxane hydrochlorideHCID 20443148—
Reactant(6aR,7S,9aS,13aS)-5-benzyloxy-2-(t-butoxycarbonyl)-2,3,6,6a,7,8,9,9a,10,11,12,13-dodecahydro-6a,7,10,10-tetramethyl-11-(1-oxa-4-azacyclohex-4-yl)imino-3-oxo-1H-benzo[8,8a][1]benzopyrano[2,3-e]isoindoleHCID 86753835—
Product(6aR,7S,9aS,13aS)-5-benzyloxy-2,3,6,6a,7,8,9,9a,10,11,12,13-dodecahydro-6a,7,10,10-tetramethyl-11-(1-oxa-4-azacyclohex-4-yl)imino-3-oxo-1H-benzo[8,8a][1]benzopyrano[2,3-e]isoindoleHCID 86753836100.4%

Reaction Steps

To the above Compound (60) (265 mg, 0.40 mmol) was added 2.0 ml of 4N HCl/dioxane solution, and the mixture stirred for one hour at room temperature. The reaction mixture was made basic with 7% aqueous sodium hydrogen carbonate solution, and extracted with ethyl acetate. The extract was concentrated under reduced pressure. The residue was purified by a silica gel column chromatography (silica gel 10 g; ethyl acetate:methanol=97:3) to give 224 mg (100%) of Compound (61).

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS05876984
Source datasetuspto-grants-1999_03
ORD IDord-7f032c1c6331410d9137276a33dd666f
Source noteuspto-grants-1999_03