Hydrochloric Acid → HCID 66980913, compound

HRID 2279243Notes

Reaction equation

HRID 2279243 reaction equation
[O:1]=[C:2]1[CH2:6][CH2:5][C@H:4]([CH2:7][O:8]C(C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[N:3]1[C:28]1[CH:35]=[CH:34][C:31]([C:32]#[N:33])=[C:30]([C:36]([F:39])([F:38])[F:37])[CH:29]=1.Cl>O1CCOCC1.O>[OH:8][CH2:7][C@H:4]1[CH2:5][CH2:6][C:2](=[O:1])[N:3]1[C:28]1[CH:35]=[CH:34][C:31]([C:32]#[N:33])=[C:30]([C:36]([F:39])([F:37])[F:38])[CH:29]=1

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 86693759HCID 86693759, compound

Product 1

HCID 66980913HCID 66980913, compoundYield 98.9%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 312751,4-DioxaneSolvent2×

Procedure

To a solution of (R)-4-(2-oxo-5-((trityloxy)methyl)pyrrolidin-1-yl)-2-(trifluoro methyl)benzonitrile 1d (3 g, 5.69 mmol) in 1,4-dioxane (30 mL), cooled to 0° C., 2M HCl in dioxane (30 mL) was added. The reaction mixture was then warmed up to room temperature and stirred for 16 h. After completion (by TLC), the reaction mixture was diluted with H2O (20 mL) and extracted with EtOAc (3×75 mL). The combined organic extracts were dried over Na2SO4 and concentrated under reduced pressure. The crude material was purified by column chromatography to afford the alcohol 1e (1.6 g, 93%) as a white solid.

Workup

  1. extractionextracted with EtOAc (3×75 mL)
  2. dry with materialThe combined organic extracts were dried over Na2SO4
  3. concentrationconcentrated under reduced pressure
  4. customThe crude material was purified by column chromatography

Sources & evidence

ORD record
ord-202138b007df4ddba8aec95b0f7db1ac
Source dataset
uspto-grants-2015_09
Patent number
US09133182B2

Reaction notes

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