Methanol → HCID 45376093, compound

HRID 1630759Notes

Reaction equation

HRID 1630759 reaction equation
F[C:2]1[N:7]=[CH:6][C:5]([CH2:8][O:9][C:10]2[N:15]=[CH:14][C:13]([CH2:16][NH:17][C@@H:18]([C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=3)[CH3:19])=[CH:12][CH:11]=2)=[CH:4][CH:3]=1.[CH3:26][O-:27].[Na+].CO.O>CCOC(C)=O>[CH3:26][O:27][C:2]1[N:7]=[CH:6][C:5]([CH2:8][O:9][C:10]2[N:15]=[CH:14][C:13]([CH2:16][NH:17][C@@H:18]([C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=3)[CH3:19])=[CH:12][CH:11]=2)=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 887MethanolHCID 962WaterHCID 10942334Sodium MethoxideHCID 45376095HCID 45376095, compound

Product 1

HCID 45376093HCID 45376093, compound

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

(1R)—N-((6-((6-Fluoro-3-pyridinyl)methoxy)-3-pyridinyl)methyl)-1-phenylethanamine (0.500 g, 1.48 mmol) was added to a microwave tube with NaOMe (0.400 g, 7.40 mmol) and MeOH (1.0 mL). The vial was sealed and irradiated for 7 min at 130° C. After the allotted time, the reaction was worked up by adding water (1.0 mL) and EtOAc (1.0 mL). The layers were separated and the aqueous layer was washed with EtOAc (3×1.0 mL). The combined organic layers were then washed with 1M sodium phosphate buffer (pH 5.5) (2×3.0 mL), dried over MgSO4, filtered, and concentrated to leave an oil. This was then purified by silica gel chromatography (1:1 hexane-EtOAc) to afford (1R)—N-((6-((6-methoxy-3-pyridinyl)methoxy)-3-pyridinyl)methyl)-1-phenylethanamine 2. MS m/z: 350 (MH+).

Workup

  1. customThe vial was sealed
  2. customirradiated for 7 min at 130° C
  3. customThe layers were separated
  4. washthe aqueous layer was washed with EtOAc (3×1.0 mL)
  5. washThe combined organic layers were then washed with 1M sodium phosphate buffer (pH 5.5) (2×3.0 mL)
  6. dry with materialdried over MgSO4
  7. filtrationfiltered
  8. concentrationconcentrated
  9. customto leave an oil
  10. customThis was then purified by silica gel chromatography (1:1 hexane-EtOAc)

Sources & evidence

ORD record
ord-98b28dd0fb9f4e70a375525edc4806b2
Source dataset
uspto-grants-2014_07
Patent number
US08791147B2

Reaction notes

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