3-Fluoro-4-methylaniline → HCID 66954619, compound

HRID 1511805Notes

Reaction equation

HRID 1511805 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH:6]=[CH:7][C:8]=1[CH3:9])[NH2:5].[O:10]([C:12](C)(C)C)[Li].[C:16]([O:20][C:21](=[O:27])[NH:22][CH2:23][C@@H:24]1[CH2:26][O:25]1)([CH3:19])([CH3:18])[CH3:17]>CN(C=O)C.CC(=O)OCC>[C:16]([O:20][C:21](=[O:27])[NH:22][CH2:23][C@H:24]1[O:25][C:12](=[O:10])[N:5]([C:4]2[CH:6]=[CH:7][C:8]([CH3:9])=[C:2]([F:1])[CH:3]=2)[CH2:26]1)([CH3:17])([CH3:18])[CH3:19]

Participants

6

Reactant 3

HCID 99573-Fluoro-4-methylanilineHCID 10464779(R)-tert-Butyl (oxiran-2-ylmethyl)carbamateHCID 178506942HCID 178506942, compound

Product 1

HCID 66954619HCID 66954619, compoundYield 81%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

According to procedure C and starting from 3-fluoro-4-methylaniline (commercial) the corresponding Cbz-protected intermediate was obtained in quantitative yields. LiOtBu (2.2M in THF, 6.8 mL, 3 eq) was added to a solution of the latter (1.3 g, 5.0 mmol) and (R)-oxiranylmethyl-carbamic acid tert-butyl ester (commercial, 0.87 g, 5.0 mmol) in DMF (10 mL). The mixture was stirred at rt over the weekend after which the solution was diluted with EA, washed with water and concentrated. The residue was purified by CC (Hept-EA 2:1) to afford the title intermediate as a colorless oil (1.32 g, 81%).

Workup

  1. customwas obtained in quantitative yields
  2. washwashed with water
  3. concentrationconcentrated
  4. customThe residue was purified by CC (Hept-EA 2:1)

Sources & evidence

ORD record
ord-2536e99328e34e9a910e5ebff18d1559
Source dataset
uspto-grants-2012_07
Patent number
US08217029B2

Reaction notes

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