Potassium Sodium Tartrate → 1-[1-(2-Fluorophenyl)cyclobutyl]methanamine

HRID 1178914Notes

Reaction equation

HRID 1178914 reaction equation
[H-].[H-].[H-].[H-].[Li+].[Al+3].[F:7][C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=1[C:14]1([C:18]#[N:19])[CH2:17][CH2:16][CH2:15]1.[C@H](O)(C([O-])=O)[C@@H](O)C([O-])=O.[Na+].[K+]>C(COC)OC>[F:7][C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=1[C:14]1([CH2:18][NH2:19])[CH2:17][CH2:16][CH2:15]1

Participants

5

Reactant 3

HCID 9357Potassium Sodium TartrateHCID 21226445Aluminium lithium hydrideHCID 227221411-(2-Fluorophenyl)cyclobutane-1-carbonitrile

Product 1

HCID 242742981-[1-(2-Fluorophenyl)cyclobutyl]methanamineYield 71%

Reagents, catalysts & solvents 1

HCID 80711,2-DimethoxyethaneSolvent

Procedure

Add LiAlH4 (461 mg, 12.1 mmol) to a solution of 1-(2-fluoro-phenyl)-cyclobutanecarbonitrile (1.38 g, 7.88 mmol) in dimethoxyethane (30 mL). Stir the solution at reflux overnight then add aq. Satd Rochelle's salt solution (30 mL) and stir for an additional 1 h at RT. Extract the mixture with CH2Cl2 (3×30 mL). Combine the organic extracts and wash with additional aq satd Rochelle's salt solution (30 mL) and brine (30 mL). Dry, filter and concentrate the organic solution then purify the crude material by flash chromatography, using 20% MeOH/CH2Cl2, to give the title compound (1 g, 71%) as a white solid. MS (ES) 180.1 (M+1)+.

Workup

  1. temperatureat reflux overnight
  2. extractionExtract the mixture with CH2Cl2 (3×30 mL)
  3. washCombine the organic extracts and wash with additional
  4. customDry
  5. filtrationfilter
  6. concentrationconcentrate the organic solution
  7. customthen purify the crude material by flash chromatography

Sources & evidence

ORD record
ord-19089e023a024d24ada43a565ac86802
Source dataset
uspto-grants-2007_10
Patent number
US07276516B2

Reaction notes

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