Pyridine → HCID 178501347, compound

HRID 244173Notes

Reaction equation

HRID 244173 reaction equation
[CH3:1][O:2][C:3]([C@H:5]1[CH2:8][C@@H:7]([OH:9])[CH2:6]1)=[O:4].N1C=CC=CC=1.[O:16](S(C1C=CC(C)=CC=1)(=O)=O)[S:17]([C:20]1[CH:26]=[CH:25][C:23]([CH3:24])=[CH:22][CH:21]=1)(=O)=[O:18].[O-][Mn](=O)(=O)=O.[K+]>CCOC(C)=O.C(Cl)Cl>[CH3:1][O:2][C:3]([C@H:5]1[CH2:8][C@@H:7]([O:9][S:17]([C:20]2[CH:26]=[CH:25][C:23]([CH3:24])=[CH:22][CH:21]=2)(=[O:18])=[O:16])[CH2:6]1)=[O:4]

Participants

7

Reactant 4

HCID 1049PyridineHCID 77773Toluene-p-sulphonic anhydrideHCID 516875Potassium PermanganateHCID 178501327HCID 178501327, compound

Product 1

HCID 178501347HCID 178501347, compound

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

An ice bath cooled methylene chloride (80.0 mL) solution of cis-3-hydroxy-cyclobutanecarboxylic acid methyl ester (4.00 g, 31.0 mmol; predominantly cis) was charged with pyridine (3.00 mL, 37.0 mmol) and Ts2O (11.1 g, 34.0 mmol). After 45 min, TLC analysis (EtOAc) revealed no starting material (KMnO4 stain for alcohol sm). The reaction mixture was concentrated in vacuo, resuspended in ether (50.0 mL) and washed with 0.5 N HCl (2×25 mL), saturated bicarbonate (2×25 mL), water (2×25 mL), brine (1×25 mL), and then dried over Na2SO4, filtered and concentrated to yield the title compound as colorless oil, predominantly cis. 1H NMR (400 MHz, CDCl3): δ=2.44-2.55 (m, 7H), 2.56-2.65 (m, 1H), 3.65 (s, 3H), 4.59-4.77 (m, 1H), 7.33 (d, 2H, J=8.0 Hz), 7.77 (d, 2H, J=8.0 Hz).

Workup

  1. concentrationThe reaction mixture was concentrated in vacuo
  2. washwashed with 0.5 N HCl (2×25 mL), saturated bicarbonate (2×25 mL), water (2×25 mL), brine (1×25 mL)
  3. dry with materialdried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-8e83aac1e43d4e19beac7b258e8dab45
Source dataset
uspto-grants-2014_02
Patent number
US08653268B2

Reaction notes

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