Tetrahydrofuran → HCID 67046468, compound

HRID 606755Notes

Reaction equation

HRID 606755 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-3-yl)-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-afa399515fb7481ab17bbb5cf2e69513
Source dataset
uspto-grants-2011_03
Patent number
US07915283B2

Reaction notes

Loading…