Tetrahydrofuran → HCID 22005217, compound

HRID 324826Notes

Reaction equation

HRID 324826 reaction equation
CO[C:3]([C:5]1[C:6]([CH:25]([CH3:27])[CH3:26])=[N:7][C:8]([CH:22]([CH3:24])[CH3:23])=[C:9](CCOC)[C:10]=1[C:11]1[CH:16]=[CH:15][C:14]([F:17])=[CH:13][CH:12]=1)=[O:4].[H-].[H-].[H-].[H-].[Li+].[Al+3].C1[CH2:38][O:37][CH2:36][CH2:35]1>>[CH:25]([C:6]1[C:5]([CH2:3][OH:4])=[C:10]([C:11]2[CH:12]=[CH:13][C:14]([F:17])=[CH:15][CH:16]=2)[C:9]([CH:36]([O:37][CH3:38])[CH3:35])=[C:8]([CH:22]([CH3:23])[CH3:24])[N:7]=1)([CH3:27])[CH3:26]

Participants

4

Reactant 3

HCID 8028TetrahydrofuranHCID 21226445Aluminium lithium hydrideHCID 22005184HCID 22005184, compound

Product 1

HCID 22005217HCID 22005217, compoundYield 85%

Procedure

The intermediate obtained in Step A (359 mg, 0.961 mmol) was dissolved in 40 mL of dry THF, for a dropwise addition of a solution of LAH (1M/THF, 1.92 mL, 2 eq.). The reaction mixture was stirred at reflux for 24 hours then cooled to room temperature and quenched with water (80 μL), 20% NaOH (80 μL), and water (160 μL). After filtration, the solvent was evaporated to afford a residue which was filtered through to a pad of silica (10% ethyl acetate/hexane) to afford the title compound as a white solid (281 mg, 0.72 mmol, 85%). 1H NMR (300 MHz, CDCl3): δ 7.13 (m, 4 H), 4.32 (dq, J=5.2 J=11.4 Hz, 1 H), 4.11 (q, J=6.3 Hz, 1 H), 3.77 (septet, J=6.6 Hz, 1 H), 3.42 (septet, J=6.6 Hz, 1 H), 3.10 (s, 3 H), 1.29 (m, 16 H). FAB-MS: calcd for (C21H28FNO2) 345, found 346 (M+H). Anal. Calcd for C21H28NO2F: C, 76.84; H, 8.69; N, 3.90. Found: C, 76.67; H, 8.76; N, 3.77. mp 151-153° C. Rf=0.4 (20% ethyl acetate/hexane).

Workup

  1. temperatureat reflux for 24 hours
  2. customquenched with water (80 μL), 20% NaOH (80 μL), and water (160 μL)
  3. filtrationAfter filtration
  4. customthe solvent was evaporated
  5. customto afford a residue which
  6. filtrationwas filtered through to a pad of silica (10% ethyl acetate/hexane)

Sources & evidence

ORD record
ord-06e84bd4eb1844b7b10cb887bc68c718
Source dataset
uspto-grants-2001_04
Patent number
US06218431B1

Reaction notes

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