HCID 66980987, compound → HCID 67130097, compound

HRID 2279249Notes

Reaction equation

HRID 2279249 reaction equation
[CH3:1][C:2]1[C:3]([C:37]([F:40])([F:39])[F:38])=[C:4]([CH:7]=[CH:8][C:9]=1[N:10]1[C@@H:14]([CH2:15][O:16]C(C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[CH2:13][CH2:12][C:11]1=[O:36])[C:5]#[N:6]>O1CCOCC1.Cl.O>[OH:16][CH2:15][C@H:14]1[CH2:13][CH2:12][C:11](=[O:36])[N:10]1[C:9]1[CH:8]=[CH:7][C:4]([C:5]#[N:6])=[C:3]([C:37]([F:40])([F:38])[F:39])[C:2]=1[CH3:1]

Participants

5

Reactant 1

HCID 66980987HCID 66980987, compound

Product 1

HCID 67130097HCID 67130097, compoundYield 79.3%

Reagents, catalysts & solvents 3

HCID 313Hydrochloric AcidSolventHCID 962WaterSolventHCID 312751,4-DioxaneSolvent2×

Procedure

To a solution of (R)-3-methyl-4-(2-oxo-5-((trityloxy)methyl)pyrrolidin-1-yl)-2-(trifluoromethyl)benzonitrile (3h) (0.48 g, 0.93 mmol) in 1,4-dioxane (15 mL), 2M HCl in 1,4-dioxane (5 mL) was added at 0° C. and stirred for 4 h. After completion of reaction (by TLC), the reaction mixture was diluted with water (20 mL) and extracted with EtOAc (2×15 mL). The combined organic extracts were washed with water (2×30 mL), dried over Na2SO4 and concentrated under reduced pressure to obtain the crude compound was purified by column chromatography to provide the alcohol 3i (0.22 g, 79%) as a white solid.

Workup

  1. customAfter completion of reaction (by TLC)
  2. extractionextracted with EtOAc (2×15 mL)
  3. washThe combined organic extracts were washed with water (2×30 mL)
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated under reduced pressure
  6. customto obtain the crude compound
  7. customwas purified by column chromatography

Sources & evidence

ORD record
ord-c4d84cfd4e3e4785ab6b4b03493e2d3d
Source dataset
uspto-grants-2015_09
Patent number
US09133182B2

Reaction notes

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