Diethyl Ether → HCID 67164894, compound

HRID 68638Notes

Reaction equation

[CH2:1]([N:4]([CH2:23][CH2:24][CH3:25])[CH2:5][CH2:6][CH2:7][CH2:8][N:9]1[CH2:18][CH2:17][C:16]2[C:11](=[CH:12][CH:13]=[C:14]([C:19](OC)=[O:20])[CH:15]=2)[CH2:10]1)[CH2:2][CH3:3].[H-].[Al+3].[Li+].[H-].[H-].[H-].O.O.O.O.O.O.O.O.O.O.S([O-])([O-])(=O)=O.[Na+].[Na+].C(OCC)C>O1CCCC1>[CH2:23]([N:4]([CH2:1][CH2:2][CH3:3])[CH2:5][CH2:6][CH2:7][CH2:8][N:9]1[CH2:18][CH2:17][C:16]2[C:11](=[CH:12][CH:13]=[C:14]([CH2:19][OH:20])[CH:15]=2)[CH2:10]1)[CH2:24][CH3:25]

Participants

Conditions

Temperature: -78 °C

Procedure

To a solution of the compound 20 (3.02 g) in tetrahydrofuran (25 mL), lithium aluminum hydride (330 mg) was, added at −78° C. The reaction mixture was stirred at −78° C. for 30 minutes. To the reaction mixture, sodium sulfate decahydrate (2.8 g) and diethylether (100 mL) were added and the temperature of the reaction mixture was raised to room temperature. The reaction mixture was filtered through Celite (trade name) and then concentrated. The residue was purified by silica gel column chromatography (ethyl acetate:methanol:triethylamine=10:1:0→10:1:0.5) to obtain the title compound (2.28 g) having the following physical properties.

Workup

additionadded at −78° C
temperaturethe temperature of the reaction mixture was raised to room temperature
filtrationThe reaction mixture was filtered through Celite (trade name)
concentrationconcentrated
customThe residue was purified by silica gel column chromatography (ethyl acetate:methanol:triethylamine=10:1:0→10:1:0.5)

Sources & evidence

ORD record: ord-ca6219708db847e196d191f4740894cb
Source dataset: uspto-grants-2014_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08822459B2

Reaction notes

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