Lithium tri-s-butylborohydride → (αR)-4-Chloro-2-fluoro-α-methylbenzenemethanamine

HRID 2359114Notes

Reaction equation

HRID 2359114 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8](=[N:10][S@](C(C)(C)C)=O)[CH3:9])=[C:4]([F:17])[CH:3]=1.C([BH-](C(CC)C)C(CC)C)(CC)C.[Li+]>C1COCC1>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C@H:8]([NH2:10])[CH3:9])=[C:4]([F:17])[CH:3]=1

Participants

4

Reactant 2

HCID 3611392Lithium tri-s-butylborohydrideHCID 86688425HCID 86688425, compound

Product 1

HCID 55252752(αR)-4-Chloro-2-fluoro-α-methylbenzenemethanamineYield 79%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a stirred solution of the crude (S)-N-(1-(4-chloro-2-fluorophenyl)ethylidene)-2-methylpropane-2-sulfinamide (6.8 g, 24.7 mmol) in THF (200 mL) at −45° C. was added a solution of lithium tri-sec-butylborohydride (L-Selectride, 1.0 M in THF, 62 mL, 61.8 mmol) dropwise. The reaction was slowly warmed to room temperature and stirred at room temperature for 18 h. The reaction mixture was concentrated in vacuo, and the crude material was purified by flash chromatography (SiO2, 25-70% ethyl acetate in hexanes) to afford the desired product as a viscous oil (5.4 g, 19.5 mmol, 79%).

Workup

  1. concentrationThe reaction mixture was concentrated in vacuo
  2. customthe crude material was purified by flash chromatography (SiO2, 25-70% ethyl acetate in hexanes)

Sources & evidence

ORD record
ord-2aa8e802783f42e68e20b785dbf3ff2b
Source dataset
uspto-grants-2014_04
Patent number
US08685959B2

Reaction notes

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