Hydrochloric Acid → HCID 66817670, compound

HRID 1754968Notes

Reaction equation

HRID 1754968 reaction equation
C[O:2][C:3](=O)[CH2:4][N:5]([C:7]1[CH:12]=[CH:11][C:10]([Br:13])=[C:9]([C:14]([F:17])([F:16])[F:15])[CH:8]=1)[CH3:6].[H-].[Al+3].[Li+].[H-].[H-].[H-].Cl>C1COCC1>[Br:13][C:10]1[CH:11]=[CH:12][C:7]([N:5]([CH3:6])[CH2:4][CH2:3][OH:2])=[CH:8][C:9]=1[C:14]([F:15])([F:16])[F:17]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 21226445Aluminium lithium hydrideHCID 66816537HCID 66816537, compound

Product 1

HCID 66817670HCID 66817670, compoundYield 82%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of [(4-bromo-3-trifluoromethyl-phenyl)-methyl-amino]-acetic acid methyl ester (77.6 mg, 0.238 mmol) in THF (1.0 ml) was added dropwise to a suspension of lithium aluminum hydride (372 mg, 2.58 mmol) in THF (1.5 ml) at 0° C. The mixture was stirred for 14 hours while gradually warming from 0° C. to room temperature. A 2 N aqueous HCl solution was added to the reaction mixture, followed by extraction with ethyl acetate. The organic layer was sequentially washed with water and saturated brine and then concentrated under reduced pressure. The resulting residue was purified by silica gel column chromatography (dichloromethane-ethyl acetate) to give 2-[(4-bromo-3-trifluoromethyl-phenyl)-methyl-amino]-ethanol (58.0 mg, 82%).

Workup

  1. temperaturewhile gradually warming from 0° C. to room temperature
  2. extractionfollowed by extraction with ethyl acetate
  3. washThe organic layer was sequentially washed with water and saturated brine
  4. concentrationconcentrated under reduced pressure
  5. customThe resulting residue was purified by silica gel column chromatography (dichloromethane-ethyl acetate)

Sources & evidence

ORD record
ord-563062ff324a492fb772c4bc679131d2
Source dataset
uspto-grants-2015_10
Patent number
US09169254B2

Reaction notes

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