Aluminium lithium hydride → (2-(2-(Dimethylamino)ethylamino)-3-fluorophenyl)methanol

HRID 1695934Notes

Reaction equation

HRID 1695934 reaction equation
[CH3:1][N:2]([CH3:17])[CH2:3][CH2:4][NH:5][C:6]1[C:15]([F:16])=[CH:14][CH:13]=[CH:12][C:7]=1[C:8](OC)=[O:9].[H-].[H-].[H-].[H-].[Li+].[Al+3]>CCOCC.[F-].[Na+].O>[CH3:1][N:2]([CH3:17])[CH2:3][CH2:4][NH:5][C:6]1[C:15]([F:16])=[CH:14][CH:13]=[CH:12][C:7]=1[CH2:8][OH:9]

Participants

6

Reactant 2

HCID 21226445Aluminium lithium hydride2×HCID 57774398Methyl 2-(2-(dimethylamino)ethylamino)-3-fluorobenzoate

Product 1

HCID 57774489(2-(2-(Dimethylamino)ethylamino)-3-fluorophenyl)methanolYield 82.1%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 3283Diethyl EtherSolvent2×HCID 5235Sodium FluorideSolvent

Conditions

Temperature
0 °C

Procedure

A solution of methyl 2-(2-(dimethylamino)ethylamino)-3-fluorobenzoate (749 mg, 3.117 mmol) in Et2O (30 mL) at −20° C. was treated with LAH (166 mg, 4.374 mmol). After 1.5 hours, additional LAH (15 mg, 0.3952 mmol) was added and the reaction was warmed to 0° C. After 1 hour at 0° C., the reaction was diluted with Et2O (70 mL) and NaF and water were added with vigorous stirring until the reaction was quenched and a white ppt formed. The clear solution was decanted and evaporated under vacuum. The crude material was purified on a 12 g ISCO redisep column (0-10% MeOH in CH2Cl2 as eluent) to yield 543 mg (82%) of (2-(2-(dimethylamino)ethylamino)-3-fluorophenyl)methanol as a clear oil. FIA: 213.08 (M+1).

Workup

  1. waitAfter 1 hour at 0° C.
  2. additionwere added
  3. customwas quenched
  4. customa white ppt formed
  5. customThe clear solution was decanted
  6. customevaporated under vacuum
  7. customThe crude material was purified on a 12 g ISCO redisep column (0-10% MeOH in CH2Cl2 as eluent)

Sources & evidence

ORD record
ord-003fd58c29cb4a338eb4198b9f86af31
Source dataset
uspto-grants-2012_04
Patent number
US08163737B2

Reaction notes

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