Oxonium, trimethyl-, tetrafluoroborate(1-) (1:1) → HCID 66733751, compound

HRID 2047213Notes

Reaction equation

HRID 2047213 reaction equation
[OH:1][CH2:2][C:3]1([NH:9][C:10](=[O:19])[O:11][CH2:12][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[CH2:8][CH2:7][O:6][CH2:5][CH2:4]1.F[B-](F)(F)F.[CH3:25][O+](C)C>C(Cl)Cl>[CH3:25][O:1][CH2:2][C:3]1([NH:9][C:10](=[O:19])[O:11][CH2:12][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[CH2:4][CH2:5][O:6][CH2:7][CH2:8]1

Participants

4

Reactant 2

HCID 2735153Oxonium, trimethyl-, tetrafluoroborate(1-) (1:1)HCID 66733669HCID 66733669, compound

Product 1

HCID 66733751HCID 66733751, compoundYield 50%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To benzyl 4-(hydroxymethyl)tetrahydro-2H-pyran-4-ylcarbamate (0.59 g, 2.23 mmol) in DCM (24 ml) was added protonsponge (0.53 g, 2.5 mmol) followed by trimethyloxoniumtetrafluoroborate (0.36 g, 2.5 mmol) at 0° C. After 20 min at 0° C., reaction mixture was warmed up to room temperature and stirred further for 16 h, at which time LC/MS confirmed full conversion of starting material to product. Reaction mixture was quenched with sat. NH1Cl and with DCM (75 ml). Organics were separated and washed with brine (20 ml) and dried over MgSO4. Solvent was removed in vacuo and the residue was purified by column chromatography on silica gel. Elution with EtOAc/Hexanes (66%-100%) gave slightly impure desired benzyl 4-(methoxymethyl)tetrahydro-2H-pyran-4-ylcarbamate (0.31 g, 50%).

Workup

  1. customreaction mixture
  2. customReaction mixture
  3. customwas quenched with sat. NH1Cl and with DCM (75 ml)
  4. customOrganics were separated
  5. washwashed with brine (20 ml)
  6. dry with materialdried over MgSO4
  7. customSolvent was removed in vacuo
  8. customthe residue was purified by column chromatography on silica gel
  9. washElution with EtOAc/Hexanes (66%-100%)

Sources & evidence

ORD record
ord-e4b208cc939b42889e56c3923eb60a6e
Source dataset
uspto-grants-2013_11
Patent number
US08591943B2

Reaction notes

Loading…