Trifluoroacetic acid → HCID 57554895, compound

HRID 1941778Notes

Reaction equation

HRID 1941778 reaction equation
C(OC([N:8]1[CH2:12][CH2:11][CH2:10][C@H:9]1[CH2:13][NH:14][C:15]1[CH:20]=[CH:19][C:18]([Cl:21])=[C:17]([O:22][CH3:23])[CH:16]=1)=O)(C)(C)C.CO[C:26]([CH3:28])=[CH2:27].FC(F)(F)C(O)=O.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>C(=O)(O)[O-].[Na+]>[Cl:21][C:18]1[CH:19]=[CH:20][C:15]([N:14]([CH:26]([CH3:28])[CH3:27])[CH2:13][C@@H:9]2[CH2:10][CH2:11][CH2:12][NH:8]2)=[CH:16][C:17]=1[O:22][CH3:23]

Participants

6

Reactant 4

HCID 6422Trifluoroacetic acidHCID 83002-MethoxypropeneHCID 5049666Sodium triacetoxyborohydrideHCID 68726870HCID 68726870, compound

Product 1

HCID 57554895HCID 57554895, compound

Reagents, catalysts & solvents 1

HCID 516892Sodium BicarbonateSolvent

Conditions

Temperature
60 °C

Procedure

To a solution of (S)-2-[(4-chloro-3-methoxy-phenylamino)-methyl]-pyrrolidine-1-carboxylic acid tert-butyl ester (0.68 g, 2.0 mmol) were added 2-methoxypropene (0.216 g, 3.0 mmol), trifluoracetic acid (0.228 g, 2.0 mmol) and sodium triacetoxyborohydride (0.64 g, 3.0 mmol). The mixture was stirred overnight at 60° C. Saturated sodium bicarbonate solution (10 ml) was added and the mixture was extracted with ethyl acetate (3×30 ml). The combined organic layers were dried with magnesium sulphate, filtered and concentrated in vacuo. The residue was dissolved in dichloromethane (3 ml) and trifluoroacetic acid (3 ml) was added. Solvent and access trifluoroacetic acid was evaporated, diisopropylethylamine (1 ml) was added to liberate the free base and the mixture was purified by flash chromatography (column: Isolute® Flash-NH2 from Separtis; eluent: ethyl acetate/heptane 1:1) to yield a light yellow oil, (0.185 g, 33%); MS (ISP): 283.5, 285.2 ((M+H)+.).

Workup

  1. extractionthe mixture was extracted with ethyl acetate (3×30 ml)
  2. dry with materialThe combined organic layers were dried with magnesium sulphate
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo
  5. dissolutionThe residue was dissolved in dichloromethane (3 ml)
  6. additiontrifluoroacetic acid (3 ml) was added
  7. customSolvent and access trifluoroacetic acid was evaporated
  8. additiondiisopropylethylamine (1 ml) was added
  9. customthe mixture was purified by flash chromatography (column: Isolute® Flash-NH2 from Separtis; eluent: ethyl acetate/heptane 1:1)
  10. customto yield a light yellow oil, (0.185 g, 33%)

Sources & evidence

ORD record
ord-54a8771353a84c98affab467009a8645
Source dataset
uspto-grants-2013_03
Patent number
US08389507B2

Reaction notes

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