HCID 18428658, compound → HCID 18428706, compound

HRID 1279633Notes

Reaction equation

HRID 1279633 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].[CH3:7][N:8]([CH2:10][C:11]1[CH:12]=[C:13]([CH:18]=[CH:19][C:20]=1[O:21][C:22]1[CH:27]=[CH:26][C:25]([C:28]([F:31])([F:30])[F:29])=[CH:24][CH:23]=1)[C:14](OC)=[O:15])[CH3:9]>C1COCC1.CCOCC>[CH3:9][N:8]([CH2:10][C:11]1[CH:12]=[C:13]([CH2:14][OH:15])[CH:18]=[CH:19][C:20]=1[O:21][C:22]1[CH:27]=[CH:26][C:25]([C:28]([F:29])([F:31])[F:30])=[CH:24][CH:23]=1)[CH3:7]

Participants

5

Reactant 2

HCID 18428658HCID 18428658, compoundHCID 21226445Aluminium lithium hydride

Product 1

HCID 18428706HCID 18428706, compoundYield 48%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of lithium aluminium hydride in THF (1 M, 7 mL, 7 mmol) was added dropwise to a stirring solution of the ester compound of Example 151 (1.66 g, 4.7 mmol) in THF (25 mL) at room temperature under nitrogen. The mixture was stirred for 3 h before being diluted with ether (100 mL) and quenched by the cautious addition of sodium hydroxide (2 M) (approximately 1 mL). The mixture was stirred for 10 min before being dried (MgSO4), filtered and concentrated in vacuo. Purification of the residue by flash chromatography {SiO2; [(MeOH/ 880 NH3) 9:1] in DCM (2% →4%)] gave the desired alcohol compound (0.7 g, 48%); Example 90: δH(CDCI3, 400 MHz) 2.13 (6 H, s), 3.39 (2 H, s), 4.70 (2 H, s), 6.93-6.98 (3 H, m), 7.30 (1 H, d), 7.52-7.56 (3 H, m); MS m/z (TS+) 326 (MH+).

Workup

  1. customquenched by the cautious addition of sodium hydroxide (2 M) (approximately 1 mL)
  2. stirringThe mixture was stirred for 10 min
  3. dry with materialbefore being dried (MgSO4)
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customPurification of the residue by flash chromatography {SiO2

Sources & evidence

ORD record
ord-d3c03ecddb1747ffb5a2389d0a451bc8
Source dataset
uspto-grants-2002_09
Patent number
US06448293B1

Reaction notes

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