Triethylammonium formate → HCID 59201542, compound

HRID 451706Notes

Reaction equation

HRID 451706 reaction equation
[F:1][C:2]1[C:22]([F:23])=[C:21]([Si](C)(C)C)[CH:20]=[C:19]([CH3:28])[C:3]=1[C:4]([C@@H:6]1[CH2:11][CH2:10][CH2:9][N:8]([C:12]([O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[O:13])[CH2:7]1)=[O:5].CCN(CC)CC.C(O)=O>C1COCC1.[Cl-].[Na+].O>[F:1][C:2]1[C:22]([F:23])=[CH:21][CH:20]=[C:19]([CH3:28])[C:3]=1[C:4]([C@@H:6]1[CH2:11][CH2:10][CH2:9][N:8]([C:12]([O:14][C:15]([CH3:17])([CH3:18])[CH3:16])=[O:13])[CH2:7]1)=[O:5]

Participants

5

Reactant 2

HCID 11084032Triethylammonium formateHCID 59201562HCID 59201562, compound

Product 1

HCID 59201542HCID 59201542, compoundYield 61%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolvent2×HCID 57417360Sodium chloride; waterSolvent

Procedure

To a solution of (R)-tert-butyl 3-(2,3-difluoro-6-methyl-4-(trimethylsilyl)benzoyl)piperidine-1-carboxylate (2 g, 4.9 mmol) in THF (20 mL) was added TEAF (0.22 g, 1.5 mmol) in THF (5 mL) at 0° C. The mixture was stirred for 4 h, after which brine was added, and the mixture was extracted with Et2O. The organic layer was washed with brine and dried over Na2SO4, concentrated. The residue was purified by column chromatography on silica gel to afford (R)-tert-butyl 3-(2,3-difluoro-6-methylbenzoyl)piperidine-1-carboxylate (1 g, 61%). 1H-NMR δ 7.07 (m, 1H), 6.90 (m, 1H), 4.10 (m, 2H), 3.92 (m, 2H), 2.21 (s, 3H), 1.97 (m, 2H), 1.60 (m, 4H), 1.49 (s, 9H), 1.30 (m, 3H).

Workup

  1. extractionthe mixture was extracted with Et2O
  2. washThe organic layer was washed with brine
  3. dry with materialdried over Na2SO4
  4. concentrationconcentrated
  5. customThe residue was purified by column chromatography on silica gel

Sources & evidence

ORD record
ord-888ea3d6ab424c2abe60b9dddfb1c9a2
Source dataset
uspto-grants-2013_07
Patent number
US08487108B2

Reaction notes

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