Pyridine → HCID 22905651, compound

HRID 1488459Notes

Reaction equation

HRID 1488459 reaction equation
[C:1]([N:6]1[C:14]2[C:9](=[C:10]([CH3:17])[C:11]([OH:16])=[C:12]([CH3:15])[CH:13]=2)[CH:8]([CH3:18])[CH2:7]1)(=[O:5])[CH:2]([CH3:4])[CH3:3].N1C=CC=CC=1.[C:25](OC(=O)C)(=[O:27])[CH3:26]>C(Cl)Cl>[C:1]([N:6]1[C:14]2[C:9](=[C:10]([CH3:17])[C:11]([O:16][C:25](=[O:27])[CH3:26])=[C:12]([CH3:15])[CH:13]=2)[CH:8]([CH3:18])[CH2:7]1)(=[O:5])[CH:2]([CH3:4])[CH3:3]

Participants

5

Reactant 3

HCID 1049PyridineHCID 7918Acetic AnhydrideHCID 22905634HCID 22905634, compound

Product 1

HCID 22905651HCID 22905651, compoundYield 77.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To an ice-cold solution of N-isobutyryl-5-hydroxy-3,4,6-trimethylindoline (11b, 49 mg, 0.2 mmol) dissolved in methylene chloride (2 mL) were added sequentially pyridine (0.16 mL, 2 mmol) and acetic anhydride (0.1 mL, 1 mmol). The mixture was stirred over the range of 0° C. to room temperature for 17 h. The mixture was diluted with methylene chloride, transferred to a separatory funnel and washed sequentially with 10% hydrochloric acid, saturated aq. sodium bicarbonate and brine. Removal of solvents after drying (MgSO4) gave a viscous liquid, which was purified by flash column chromatography, using 1:4 ethyl acetate:hexanes as eluent, to afford the N-isobutyryl-5-acetoxy-3,4,6-trimethylindoline (12b, 45 mg, 77% yield) as a colorless solid, mp 118°-120° C. Spectral data: 1H NMR: δ 2.0 (s, 3H), 2.06 (s, 3H), 2.26 (s, 3H), 2.7 (quintet, 1H, J=6.7 Hz), 3.3 (t, 1H, J=6.7 Hz), 3.7 (dd, 1H, J=10.2, 1.2 Hz), 4.1 (t, 1H, J=9.3 Hz), 8.0 (s, 1H); CI-HRMS: calcd. for C17H24NO3 (M+H+) 290.1756, fnd. 290.1756.

Workup

  1. customtransferred to a separatory funnel
  2. washwashed sequentially with 10% hydrochloric acid, saturated aq. sodium bicarbonate and brine
  3. customRemoval of solvents
  4. dry with materialafter drying (MgSO4)
  5. customgave a viscous liquid, which
  6. customwas purified by flash column chromatography

Sources & evidence

ORD record
ord-81a129f0b3fd46ee8875511fe82a9371
Source dataset
uspto-grants-1997_10
Patent number
US05674876

Reaction notes

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