1,3-Difluoroacetone → HCID 67170709, compound

HRID 706909Notes

Reaction equation

HRID 706909 reaction equation
[NH:1]1[CH2:6][CH2:5][CH:4]([CH2:7][OH:8])[CH2:3][CH2:2]1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].[F:23][CH2:24][C:25](=O)[CH2:26][F:27].C([O-])(O)=O.[Na+]>ClCCl>[F:23][CH2:24][CH:25]([N:1]1[CH2:6][CH2:5][CH:4]([CH2:7][OH:8])[CH2:3][CH2:2]1)[CH2:26][F:27]

Participants

6

Reactant 4

HCID 2283971,3-DifluoroacetoneHCID 4207714-PiperidinemethanolHCID 516892Sodium BicarbonateHCID 5049666Sodium triacetoxyborohydride

Product 1

HCID 67170709HCID 67170709, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A suspension of piperidin-4-ylmethanol (0.250 g), sodium triacetoxyborohydride (0.690 g) and 1,3-difluoropropan-2-one (0.245 g) were stirred together in dichloromethane. After stirring overnight the reaction was poured into saturated aqueous NaHCO3 solution (10 mL) and stirred for 15 minutes. The reaction was extracted with dichloromethane (3×25 mL), dried over magnesium sulfate, filtered, and concentrated. Silica gel chromatography (GraceResolv 12 g) eluting with a gradient of 0.75% to 3% methanol/dichloromethane gave the title compound.

Workup

  1. stirringstirred for 15 minutes
  2. extractionThe reaction was extracted with dichloromethane (3×25 mL)
  3. dry with materialdried over magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated
  6. washSilica gel chromatography (GraceResolv 12 g) eluting with a gradient of 0.75% to 3% methanol/dichloromethane

Sources & evidence

ORD record
ord-ffa52eddf9b0405cad97d6776accc8c4
Source dataset
uspto-grants-2015_11
Patent number
US09174982B2

Reaction notes

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