Trifluoroacetic acid → [4-((R)-2-hydroxymethyl-6-oxo-piperidin-1-yl)-but-2-ynyloxy]-acetonitrile

HRID 349371Notes

Reaction equation

HRID 349371 reaction equation
FC(F)(F)C(O)=O.C(OC([O:13][CH2:14][C@H:15]1[CH2:20][CH2:19][CH2:18][C:17](=[O:21])[N:16]1[CH2:22][C:23]#[C:24][CH2:25][O:26][CH2:27][C:28]#[N:29])C)C>C(Cl)Cl>[OH:13][CH2:14][C@H:15]1[CH2:20][CH2:19][CH2:18][C:17](=[O:21])[N:16]1[CH2:22][C:23]#[C:24][CH2:25][O:26][CH2:27][C:28]#[N:29]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 69021582{4-[(R)-2-(1-ethoxy-ethoxymethyl)-6-oxo-piperidin-1-yl]-but-2-ynyloxy}-acetonitrile

Product 1

HCID 69022423[4-((R)-2-hydroxymethyl-6-oxo-piperidin-1-yl)-but-2-ynyloxy]-acetonitrileYield 53.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Trifluoroacetic acid (0.5 mL, 6.5 mmol) was added to a solution of {4-[(R)-2-(1-ethoxy-ethoxymethyl)-6-oxo-piperidin-1-yl]-but-2-ynyloxy}-acetonitrile (290 mg, 0.94 mmol) in CH2Cl2 (3 mL). After 1 h at rt, the reaction mixture was quenched with saturated aqueous NaHCO3 (20 mL) and extracted with CH2Cl2 (3×20 mL). Combined extracts were dried (Na2SO4), filtered and concentrated in vacuo. Purification of the residue by flash column chromatography on silica gel (CH2Cl2→3% MeOH/CH2Cl2, gradient) afforded 118 mg (53%) of [4-((R)-2-hydroxymethyl-6-oxo-piperidin-1-yl)-but-2-ynyloxy]-acetonitrile.

Workup

  1. customthe reaction mixture was quenched with saturated aqueous NaHCO3 (20 mL)
  2. extractionextracted with CH2Cl2 (3×20 mL)
  3. dry with materialCombined extracts were dried (Na2SO4)
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customPurification of the residue by flash column chromatography on silica gel (CH2Cl2→3% MeOH/CH2Cl2, gradient)

Sources & evidence

ORD record
ord-dcd0c876b2524b22bfc91d02dcedd3a8
Source dataset
uspto-grants-2007_02
Patent number
US07179820B2

Reaction notes

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