1,3-Difluoroacetone → HCID 67170709, compound

HRID 2040175Notes

Reaction equation

HRID 2040175 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-04717e2ad2bf4b7894aa5be163b1d952
Source dataset
uspto-grants-2013_11
Patent number
US08580794B2

Reaction notes

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