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

HRID 1747157Notes

Reaction equation

HRID 1747157 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-565fd7a762ad469a83637119da1e637f
Source dataset
uspto-grants-2015_10
Patent number
US09150550B2

Reaction notes

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