Methylamine → t-Butyl 2-(2-(4-fluoro-3-(methylsulfonyl)phenyl)-4-((methylamino)methyl)phenoxy)acetate

HRID 68611Notes

Reaction equation

HRID 68611 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:22]=[C:21]([CH:23]=O)[CH:20]=[CH:19][C:9]=2[O:10][CH2:11][C:12]([O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[O:13])=[CH:4][C:3]=1[S:25]([CH3:28])(=[O:27])=[O:26].[CH3:29][NH2:30].C1COCC1.[BH4-].[Na+]>CO.O>[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:22]=[C:21]([CH2:23][NH:30][CH3:29])[CH:20]=[CH:19][C:9]=2[O:10][CH2:11][C:12]([O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[O:13])=[CH:4][C:3]=1[S:25]([CH3:28])(=[O:27])=[O:26]

Participants

7

Reactant 4

HCID 6329MethylamineHCID 8028TetrahydrofuranHCID 4311764Sodium borohydrideHCID 86681841t-Butyl 2-(2-(4-fluoro-3-(methylsulfonyl)phenyl)-4-formylphenoxy)acetate

Product 1

HCID 67528897t-Butyl 2-(2-(4-fluoro-3-(methylsulfonyl)phenyl)-4-((methylamino)methyl)phenoxy)acetateYield 93%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

Intermediate 29 (270 mg, 0.66 mmol, 1 eq) was stirred with methylamine (1.5 mL of a 0.88 M THF solution, 1.32 mmol, 2 eq.) in MeOH for 2 h. Sodium borohydride (50 mg, 0.66 mmol, 1 eq.) was added, and the resulting mixture was stirred at room temperature for an additional 2 h. Water (3 mL) was added and the MeOH was removed in vacuo. The resulting solution was extracted with EtOAc, dried (Na2SO4), and concentrated in vacuo to give 260 mg (93%) of t-butyl 2-(2-(4-fluoro-3-(methylsulfonyl)phenyl)-4-((methylamino)methyl)phenoxy)acetate (30) as oil.

Workup

  1. customthe MeOH was removed in vacuo
  2. extractionThe resulting solution was extracted with EtOAc
  3. dry with materialdried (Na2SO4)
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-e09bf489577d49e79637365a98b2a8a0
Source dataset
uspto-grants-2014_09
Patent number
US08822467B2

Reaction notes

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