Water → HCID 67974807, compound

HRID 508620Notes

Reaction equation

HRID 508620 reaction equation
C([O:3][C:4](=O)[CH2:5][CH2:6][C:7]1[CH:11]=[C:10]([C:12]2[CH:17]=[CH:16][C:15]([CH3:18])=[CH:14][CH:13]=2)[N:9]([C:19]2[CH:24]=[CH:23][C:22]([S:25](=[O:28])(=[O:27])[NH2:26])=[CH:21][CH:20]=2)[N:8]=1)C.[H-].[H-].[H-].[H-].[Li+].[Al+3].O>C1COCC1>[OH:3][CH2:4][CH2:5][CH2:6][C:7]1[CH:11]=[C:10]([C:12]2[CH:13]=[CH:14][C:15]([CH3:18])=[CH:16][CH:17]=2)[N:9]([C:19]2[CH:24]=[CH:23][C:22]([S:25]([NH2:26])(=[O:28])=[O:27])=[CH:21][CH:20]=2)[N:8]=1

Participants

5

Reactant 3

HCID 962WaterHCID 21226445Aluminium lithium hydrideHCID 67976211HCID 67976211, compound

Product 1

HCID 67974807HCID 67974807, compoundYield 81%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of ester 17c (0.11 g, 0.27 mmol) in 5 mL of THF was added LiAlH4 (32 mg, 0.85 mmol). The reaction mixture was stirred for 6 hours at room temperature. EtOAC (10 mL) and water (5 mL) were added successively. The solvent was removed in vacuo and the resulting solid was filtered. The crude product was purified by column chromatography (EtOAc/Hexanes in adequate proportions) to give the titled compound (80 mg, 81%) as a white solid. mp 123.4-125.6° C. 1H NMR (300 MHz, DMSO-d6): δ 7.79 (d, J=9 Hz, 2H), 7.47-7.42 (m, 2H), 7.39 (d, J=9 Hz, 2H), 7.20 (d, J=8 Hz, 2H), 7.13 (d, J=8 Hz, 2H), 6.49 (s, 1H), 4.52 (t, J=5 Hz, 1H), 3.53-3.45 (m, 2H), 2.73-2.59 (m, 2H), 2.31 (s, 3H), 1.87-1.75 (m, 2H).

Workup

  1. customThe solvent was removed in vacuo
  2. filtrationthe resulting solid was filtered
  3. customThe crude product was purified by column chromatography (EtOAc/Hexanes in adequate proportions)

Sources & evidence

ORD record
ord-6d8cc760488144a5a400dfefd8528e5a
Source dataset
uspto-grants-2015_08
Patent number
US09096532B2

Reaction notes

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