Aluminium lithium hydride → (2-(2-Morpholinoethylamino)-3-fluorophenyl)methanol

HRID 1695941Notes

Reaction equation

[O:1]1[CH2:6][CH2:5][N:4]([CH2:7][CH2:8][NH:9][C:10]2[C:19]([F:20])=[CH:18][CH:17]=[CH:16][C:11]=2[C:12](OC)=[O:13])[CH2:3][CH2:2]1.[H-].[H-].[H-].[H-].[Li+].[Al+3]>CCOCC>[O:1]1[CH2:6][CH2:5][N:4]([CH2:7][CH2:8][NH:9][C:10]2[C:19]([F:20])=[CH:18][CH:17]=[CH:16][C:11]=2[CH2:12][OH:13])[CH2:3][CH2:2]1

Participants

Conditions

Temperature: 0 °C

Procedure

Methyl 2-(2-morpholinoethylamino)-3-fluorobenzoate (943 mg, 3.340 mmol) was dissolved in Et2O (˜40 mL) and cooled to 0° C. The mixture was treated with LAH (203 mg, 5.35 mmol) and stirred at 0° C. The reaction was quenched with NaF (5 g) and water (5 mL), then decanted, dried over Na2SO4, and solvent was removed under vacuum. The mixture was diluted with CH2Cl2 and EtOAc, dried over MgSO4, filtered and the solvent was evaporated. The crude product was purified on an ISCO system with EtOAc/Hex (20-80% over 20 column volumes on 12 g redisep column) to give (2-(2-morpholinoethylamino)-3-fluorophenyl)methanol (661 mg, 2.599 mmol) as a colorless oil.

Workup

customThe reaction was quenched with NaF (5 g) and water (5 mL)
customdecanted
dry with materialdried over Na2SO4, and solvent
customwas removed under vacuum
additionThe mixture was diluted with CH2Cl2 and EtOAc
dry with materialdried over MgSO4
filtrationfiltered
customthe solvent was evaporated
customThe crude product was purified on an ISCO system with EtOAc/Hex (20-80% over 20 column volumes on 12 g redisep column)

Sources & evidence

ORD record: ord-96822272c8dc4379a27e30a462bb5c1d
Source dataset: uspto-grants-2012_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08163737B2

Reaction notes

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