Acetic Acid → 7-[1-(3-Methoxycarbonylpyridin-4-yl)piperidin-4-ylmethoxy]-1,2,3,4-tetrahydroisoquinoline-2-carboxylic acid tert-butyl ester

HRID 412576Notes

Reaction equation

HRID 412576 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:17][CH2:16][C:15]2[C:10](=[CH:11][C:12]([O:18][CH2:19][CH:20]3[CH2:25][CH2:24][N:23]([C:26]4[CH:31]=[CH:30][N:29]=[CH:28][C:27]=4[CH:32]=[O:33])[CH2:22][CH2:21]3)=[CH:13][CH:14]=2)[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[C-]#N.[Na+].[C:37](O)(=[O:39])C>C(Cl)(Cl)Cl.CO.[O-2].[O-2].[Mn+4]>[C:1]([O:5][C:6]([N:8]1[CH2:17][CH2:16][C:15]2[C:10](=[CH:11][C:12]([O:18][CH2:19][CH:20]3[CH2:21][CH2:22][N:23]([C:26]4[CH:31]=[CH:30][N:29]=[CH:28][C:27]=4[C:32]([O:39][CH3:37])=[O:33])[CH2:24][CH2:25]3)=[CH:13][CH:14]=2)[CH2:9]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

7

Reactant 3

HCID 176Acetic AcidHCID 8929Sodium CyanideHCID 112017967-[1-(3-Formylpyridin-4-yl)piperidin-4-ylmethoxy]-1,2,3,4-tetrahydroisoquinoline-2-carboxylic acid tert-butyl ester

Product 1

HCID 112024757-[1-(3-Methoxycarbonylpyridin-4-yl)piperidin-4-ylmethoxy]-1,2,3,4-tetrahydroisoquinoline-2-carboxylic acid tert-butyl ester

Reagents, catalysts & solvents 3

HCID 178418406HCID 178418406, compoundCatalystHCID 887MethanolSolventHCID 6212ChloroformSolvent

Procedure

To a soution of 7-[1-(3-formylpyridin-4-yl)piperidin4-ylmethoxy]-1,2,3,4-tetrahydroisoquinoline-2-carboxylic acid tert-butyl ester (50 mg) in a mixture of chloroform (0.5 ml) and methanol (0.2 ml) were added sodium cyanide (8 mg), manganese dioxide (250 mg) and acetic acid (0.003 ml), and the mixture was stirred at room temperature for 12 hours. After completion of the reaction, the reaction mixture was filtrated and the solvent was evaporated. The obtained residue was purified by preparative thin layer chromatography (chloroform:methanol=15:1) and dried under reduced pressure to give the title compound (50 mg).

Workup

  1. customAfter completion of the reaction
  2. filtrationthe reaction mixture was filtrated
  3. customthe solvent was evaporated
  4. customThe obtained residue was purified by preparative thin layer chromatography (chloroform:methanol=15:1)
  5. customdried under reduced pressure

Sources & evidence

ORD record
ord-bb5dcad631774167b7b592a920ea4bb6
Source dataset
uspto-grants-2003_05
Patent number
US06562828B1

Reaction notes

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