Tetrahydrofuran → HCID 67046468, compound

HRID 1394436Notes

Reaction equation

HRID 1394436 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][C:11](=[C:14]([C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)[C:15]2[CH:16]=[N:17][CH:18]=[C:19]([CH2:21]CC(O)=O)[CH:20]=2)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[H-].[H-].[H-].[H-].[Li+].[Al+3].C1C[O:41]CC1>>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][C:11](=[C:14]([C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)[C:15]2[CH:16]=[N:17][CH:18]=[C:19]([CH2:21][OH:41])[CH:20]=2)[CH2:10][CH2:9]1)=[O:7])([CH3:3])([CH3:2])[CH3:4]

Participants

4

Reactant 3

HCID 8028TetrahydrofuranHCID 21226445Aluminium lithium hydrideHCID 67046508HCID 67046508, compound

Product 1

HCID 67046468HCID 67046468, compoundYield 87%

Procedure

To a solution of 4-(1-phenyl-1-(5-carboxyethylpyridin-3yl)-methylene)-piperidine-1-carboxylic acid tert-butyl ester (0.058 g, 0.137 mmol) in dry THF (2 mL) was added LAH (0.334 mL, 0.949 mmol) portionwise over 10 min. The mixture was stirred at room temperature for an additional 30 min and then it was quenched with a saturated aqueous solution of Rochelle's salt (5 mL). The resulting mixture was filtered and the filtrate concentrated to dryness to give the title compound (0.046 g, 87%) as a clear brown oil:

Workup

  1. customit was quenched with a saturated aqueous solution of Rochelle's salt (5 mL)
  2. filtrationThe resulting mixture was filtered
  3. concentrationthe filtrate concentrated to dryness

Sources & evidence

ORD record
ord-6ca9d4b189ab4c2abd64e15714bf2104
Source dataset
uspto-grants-2008_03
Patent number
US07348337B2

Reaction notes

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