O-Cresol → HCID 42644120, compound

HRID 1809089Notes

Reaction equation

HRID 1809089 reaction equation
[OH:1][CH2:2][C:3]1[S:7][CH:6]=[C:5]([C:8]([N:10]2[CH2:15][CH2:14][CH2:13][CH2:12][CH2:11]2)=[O:9])[CH:4]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.CCOC(/N=N/C(OCC)=O)=O.[CH3:47][C:48]1[CH:53]=[CH:52][CH:51]=[CH:50][C:49]=1O>C1COCC1>[N:10]1([C:8]([C:5]2[CH:4]=[C:3]([CH2:2][O:1][C:49]3[CH:50]=[CH:51][CH:52]=[CH:53][C:48]=3[CH3:47])[S:7][CH:6]=2)=[O:9])[CH2:11][CH2:12][CH2:13][CH2:14][CH2:15]1

Participants

6

Reactant 4

HCID 335O-CresolHCID 11776TriphenylphosphineHCID 5462977Diethyl azodicarboxylateHCID 59542586HCID 59542586, compound

Product 1

HCID 42644120HCID 42644120, compoundYield 21.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

(5-Hydroxymethyl-thiophen-3-yl)-piperidin-1-yl-nnethanone (0.068 g, 0.3 mmol) was dissolved in THF (5 mL). Triphenylphosphine (0.3 mmol), diethylazodicarboxylate (0.3 mmol) and 2-methyl-phenol (0.3 mmol) were added and the reaction stirred overnight. The reaction was quenched with saturated aqueous ammonium chloride and the solvent was reduced under vacuum. The residue was partitioned between DCM and water and the organic solution separated, dried over magnesium sulphate, filtered and the solvent evaporated. The product was purified by HPLC, eluting with acetonitrile in water (0.1% formic acid). The fractions containing the desired product were concentrated under vacuum to give the title compound (20 mg). LCMS m/z 316.20 [M+H]+RT=11.75 min (Analytical Method 1). 1H NMR (400 MHz, CHCl3-d): δ 7.45 (s, 1H), 7.2-7.1 (m, 3H), 6.9 (m, 2H), 5.2 (s, 2H), 3.6 (m, 4H), 2.25 (s, 3H), 1.7-1.6 (m, 6H).

Workup

  1. customThe reaction was quenched with saturated aqueous ammonium chloride
  2. customThe residue was partitioned between DCM and water
  3. customthe organic solution separated
  4. dry with materialdried over magnesium sulphate
  5. filtrationfiltered
  6. customthe solvent evaporated
  7. customThe product was purified by HPLC
  8. washeluting with acetonitrile in water (0.1% formic acid)
  9. additionThe fractions containing the desired product
  10. concentrationwere concentrated under vacuum

Sources & evidence

ORD record
ord-d7b2cad039164b4c93e48d1b210a669e
Source dataset
uspto-grants-2013_01
Patent number
US08362008B2

Reaction notes

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