Water → HCID 69593509, compound

HRID 1790428Notes

Reaction equation

[H-].[Al+3].[Li+].[H-].[H-].[H-].[C:7]([N:10]1[CH2:15][CH2:14][C@@H:13]([N:16]2[C:24]3[C:19](=[CH:20][CH:21]=[CH:22][CH:23]=3)[CH2:18][CH2:17]2)[C@H:12]([C:25](OCC)=[O:26])[CH2:11]1)(=O)[CH3:8].O.[OH-].[Na+]>O1CCCC1.C(OCC)(=O)C>[CH2:7]([N:10]1[CH2:15][CH2:14][C@@H:13]([N:16]2[C:24]3[C:19](=[CH:20][CH:21]=[CH:22][CH:23]=3)[CH2:18][CH2:17]2)[C@H:12]([CH2:25][OH:26])[CH2:11]1)[CH3:8]

Participants

Conditions

Temperature: 0 °C

Procedure

In a stream of nitrogen, lithium aluminum hydride (133 mg) was carefully added to dry tetrahydrofuran (5 ml) under ice cooling. To the resultant mixture was gradually added a solution of trans-1-(1-acetyl-3-ethoxycarbonylpiperidin-4-yl)indoline (850 mg) in dry tetrahydrofuran (5 ml) and the resulting mixture was stirred at 0° C. overnight. Under ice cooling and vigorous stirring, water (0.13 ml), a 5 N aqueous solution (0.13 ml) of sodium hydroxide and further water (0.4 ml) were successively added thereto. After allowing to warm the resultant mixture to room temperature, ethyl acetate (30 ml) was added thereto followed by drying over anhydrous sodium sulfate. After filtering and concentrating under reduced pressure, the resulting residue was purified by silica gel column chromatography (methylene chloride/methanol system) to give the title compound (340 mg) as a pale yellow powder (yield: 49%).

Workup

dry with materialby drying over anhydrous sodium sulfate
filtrationAfter filtering
concentrationconcentrating under reduced pressure
customthe resulting residue was purified by silica gel column chromatography (methylene chloride/methanol system)

Sources & evidence

ORD record: ord-85ab805df84f412a9fe3c4095e8a3069
Source dataset: uspto-grants-2006_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07071201B2

Reaction notes

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