Ammonium Chloride → HCID 90016006, compound

HRID 920148Notes

Reaction equation

HRID 920148 reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][C:5]([F:22])=[C:6]([C@:8]([NH:15]C(=O)C(F)(F)F)([CH3:14])[CH2:9][S:10][CH2:11][C:12]#[N:13])[CH:7]=1.[BH4-].[Na+].[NH4+].[Cl-]>C(O)C>[NH2:15][C@@:8]([C:6]1[CH:7]=[C:2]([Br:1])[CH:3]=[CH:4][C:5]=1[F:22])([CH3:14])[CH2:9][S:10][CH2:11][C:12]#[N:13]

Participants

5

Reactant 3

HCID 25517Ammonium ChlorideHCID 4311764Sodium borohydrideHCID 90016379HCID 90016379, compound

Product 1

HCID 90016006HCID 90016006, compoundYield 53.7%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
23 °C

Procedure

To a solution of (R)—N-(2-(5-bromo-2-fluorophenyl)-1-(cyanomethylthio)propan-2-yl)-2,2,2-trifluoroacetamide (3 g, 6.76 mmol, Eq: 1.00) in ethanol (30 ml) was added sodium borohydride (1.02 g, 27.1 mmol, Eq: 4.0) and the mixture was stirred at 23° C. for 16 hours. Poured into icecold sat. NH4Cl-sol., stirred for 10 min and extracted twice with ethyl acetate. The combined organic layers were dried over Na2SO4, filtered and evaporated. The residue was purified by silica gel column chromatography with 0 to 50% ethyl acetate in heptane to give the (R)-2-(2-amino-2-(5-bromo-2-fluorophenyl)propylthio)acetonitrile (1.1 g, 3.63 mmol, 53.6% yield) as a light yellow oil. MS (ISP): m/z=303.0 [M+H]+ and 304.9 [M+2+H]+.

Workup

  1. stirring, stirred for 10 min
  2. extractionextracted twice with ethyl acetate
  3. dry with materialThe combined organic layers were dried over Na2SO4
  4. filtrationfiltered
  5. customevaporated
  6. customThe residue was purified by silica gel column chromatography with 0 to 50% ethyl acetate in heptane

Sources & evidence

ORD record
ord-81f3f23c0de242ed9bf35ec32a73ff3e
Source dataset
uspto-grants-2016_03
Patent number
US09273042B2

Reaction notes

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