o-Fluorobenzaldehyde → HCID 89650132, compound

HRID 1479036Notes

Reaction equation

HRID 1479036 reaction equation
C(O[K])(C)(C)C.[C:7]([O:11][C:12](=[O:18])[N:13]([CH2:15][CH2:16][OH:17])[CH3:14])([CH3:10])([CH3:9])[CH3:8].F[C:20]1[CH:27]=[CH:26][CH:25]=[CH:24][C:21]=1[CH:22]=[O:23]>O1CCOCC1>[C:7]([O:11][C:12](=[O:18])[N:13]([CH2:15][CH2:16][O:17][C:20]1[CH:27]=[CH:26][CH:25]=[CH:24][C:21]=1[CH:22]=[O:23])[CH3:14])([CH3:10])([CH3:8])[CH3:9]

Participants

5

Reactant 3

HCID 67970o-FluorobenzaldehydeHCID 545700N-(tert-Butoxycarbonyl)-N-methyl-2-aminoethanolHCID 178418922HCID 178418922, compound

Product 1

HCID 89650132HCID 89650132, compoundYield 29%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

tBuOK (2.69 g; 24 mmol; 1.2 eq.) was added portionwise to a solution of (2-hydroxy-ethyl)-methyl-carbamic acid tert-butyl ester (3.5 g; 20 mmol; 1 eq.) and 2-fluoro-benzaldehyde (2.97 g; 24 mmol; 1.2 eq.) in 1,4-dioxane (30 mL) and the reaction mixture was stirred at room temperature for 20 minutes. After dilution with EA, the solution was washed with water (2×) then brine, dried over magnesium sulfate and concentrated in vacuo. Purification by column chromatography (15% to 50% EA in cyclohexane) afforded the title compound (1.6 g, 29%) as a colourless oil. HPLC (max plot) 89.3%; Rt 4.21 min.

Workup

  1. washAfter dilution with EA, the solution was washed with water (2×)
  2. dry with materialbrine, dried over magnesium sulfate
  3. concentrationconcentrated in vacuo
  4. customPurification by column chromatography (15% to 50% EA in cyclohexane)

Sources & evidence

ORD record
ord-74e1ba7003e5409391903cea7c45a5f8
Source dataset
uspto-grants-2016_08
Patent number
US09403835B2

Reaction notes

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