HCID 10321357, compound → HCID 86746897, compound

HRID 1587012Notes

Reaction equation

HRID 1587012 reaction equation
C[O:2][C:3]([C:5]1[CH:6]([C:24]2[CH:29]=[CH:28][C:27]([O:30][CH3:31])=[C:26]([O:32][CH3:33])[CH:25]=2)[C:7]([C:22]#[N:23])=[C:8]([CH3:21])[N:9]([CH2:12][CH2:13][CH2:14][C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[C:10]=1[CH3:11])=O.[H-].[H-].[H-].[H-].[Li+].[Al+3].C(OCC)C>O1CCCC1>[CH3:33][O:32][C:26]1[CH:25]=[C:24]([C:6]2[C:5]([CH2:3][OH:2])=[C:10]([CH3:11])[N:9]([CH2:12][CH2:13][CH2:14][C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=3)[CH:8]([CH3:21])[C:7]=2[C:22]#[N:23])[CH:29]=[CH:28][C:27]=1[O:30][CH3:31]

Participants

4

Reactant 2

HCID 10321357HCID 10321357, compoundHCID 22110940HCID 22110940, compound

Product 1

HCID 86746897HCID 86746897, compoundYield 78%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 1.48 g (3.32 mmol) of 1.4-dihydro-4-(3,4-dimethoxyphenyl)-2,6-dimethyl -1-(3-phenylpropyl)-3-cyano-5-pyridine carboxylic acid-5-methylester in 42 ml of dry tetrahydrofuran (THF) was added with stirring 1.8 ml of 1N LiAlH4 /diethyl ether solution at room temperature (about 20°-30° C.). The mixture was stirred for 20 min. and was poured into ice-water. The mixture was filtered and extracted with CH2Cl2. This oil was purified by column chromatography (AcOEt:Hexane 1:1) to give 1.08 g (2.58 mmol) of 1,4-dihydro-4-(3,4-dimethoxyphenyl-2,6-dimethyl -1-(3-phenylpropyl)-3-cyano-5-hydroxymethylpyridine (78% yield: oil).

Workup

  1. filtrationThe mixture was filtered
  2. extractionextracted with CH2Cl2
  3. customThis oil was purified by column chromatography (AcOEt:Hexane 1:1)

Sources & evidence

ORD record
ord-145669db049442b3896632caef59b8b6
Source dataset
uspto-grants-1993_06
Patent number
US05216172

Reaction notes

Loading…