Lithium borohydride → 4-(3,3''-dimethyl-3',4',5',6'-tetrahydro-2'H-[2,2'; 6',2'']terpyridin-1'-ylmethyl)-3-hydroxymethyl-benzonitrile

HRID 1784188Notes

Reaction equation

HRID 1784188 reaction equation
C[O:2][C:3](=O)[C:4]1[CH:9]=[C:8]([C:10]#[N:11])[CH:7]=[CH:6][C:5]=1[CH2:12][N:13]1[CH:18]([C:19]2[C:24]([CH3:25])=[CH:23][CH:22]=[CH:21][N:20]=2)[CH2:17][CH2:16][CH2:15][CH:14]1[C:26]1[C:31]([CH3:32])=[CH:30][CH:29]=[CH:28][N:27]=1.[Li+].[BH4-]>CO>[CH3:25][C:24]1[C:19]([CH:18]2[CH2:17][CH2:16][CH2:15][CH:14]([C:26]3[C:31]([CH3:32])=[CH:30][CH:29]=[CH:28][N:27]=3)[N:13]2[CH2:12][C:5]2[CH:6]=[CH:7][C:8]([C:10]#[N:11])=[CH:9][C:4]=2[CH2:3][OH:2])=[N:20][CH:21]=[CH:22][CH:23]=1

Participants

4

Reactant 2

HCID 4148881Lithium borohydrideHCID 674204965-cyano-2-(3,3''-dimethyl-3',4',5',6'-tetrahydro-2'H-[2,2'; 6',2'']terpyridin-1'-ylmethyl)-benzoic acid methyl ester

Product 1

HCID 674215664-(3,3''-dimethyl-3',4',5',6'-tetrahydro-2'H-[2,2'; 6',2'']terpyridin-1'-ylmethyl)-3-hydroxymethyl-benzonitrileYield 86%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a stirred, room temperature solution of the ester from above (2.05 g, 4.6 mmol) in MeOH (50 mL) was added LiBH4 (1.0 g, 50 mmol) in three portions. Effervescence was observed, and the mixture was stirred for 3.5 hours. The mixture was concentrated and 1 N NaOH (50 mL) was added to the resultant residue. The aqueous mixture was extracted with CH2Cl2 (3×50 mL). The organic extracts were combined, dried (Na2SO4), and concentrated. Purification of the crude material by column chromatography on silica gel (40 g, eluted with 5% NH4OH/5% MeOH/CH2Cl2) provided 4-(3,3″-dimethyl-3′,4′,5′,6′-tetrahydro-2′H-[2,2′;6′,2″]terpyridin-1′-ylmethyl)-3-hydroxymethyl-benzonitrile (1.63 g, 86%) as a pale yellow solid.

Workup

  1. concentrationThe mixture was concentrated
  2. addition1 N NaOH (50 mL) was added to the resultant residue
  3. extractionThe aqueous mixture was extracted with CH2Cl2 (3×50 mL)
  4. dry with materialdried (Na2SO4)
  5. concentrationconcentrated
  6. customPurification of the crude material by column chromatography on silica gel (40 g, eluted with 5% NH4OH/5% MeOH/CH2Cl2)

Sources & evidence

ORD record
ord-a9159759d5ba40b1905a655940fbe6f2
Source dataset
uspto-grants-2009_03
Patent number
US07501518B2

Reaction notes

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