Methanol → HCID 69880756, compound

HRID 392430Notes

Reaction equation

HRID 392430 reaction equation
C[O:2][C:3]([C:5]1[CH:10]=[CH:9][C:8]([NH:11][CH2:12][C:13]2[CH:14]=[N:15][CH:16]=[CH:17][CH:18]=2)=[CH:7][CH:6]=1)=O.CC(C[AlH]CC(C)C)C.CO>C1COCC1.CCOCC.[C@H](O)(C([O-])=O)[C@@H](O)C([O-])=O.[Na+].[K+]>[OH:2][CH2:3][C:5]1[CH:6]=[CH:7][C:8]([NH:11][CH2:12][C:13]2[CH:14]=[N:15][CH:16]=[CH:17][CH:18]=2)=[CH:9][CH:10]=1

Participants

7

Reactant 3

HCID 887MethanolHCID 14487Diisobutylaluminum hydrideHCID 43112089HCID 43112089, compound

Product 1

HCID 69880756HCID 69880756, compoundYield 95.1%

Reagents, catalysts & solvents 3

HCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolventHCID 9357Potassium Sodium TartrateSolvent

Conditions

Temperature
0 °C

Procedure

To a −78° C. solution of N-(4-methoxycarbonylphenyl) pyrid-3-ylmethylamine (105 g, 0.433 moles, leg) in THF (17 volumes) was added slowly DIBAl-H (1M in toluene, 1084 mL, 1.084 moles, 2.5 eq,) and held cold for 1 hour. The reaction was then allowed to warm to 0° C. for 2 h. The reaction was carefully quenched with methanol (1.8 eq). It was then diluted with ether (62 volumes) and Saturated Rochelle's salt (37 volumes) and stirred vigorously overnight. The layers were separated and the aqueous extracted with EtOAc. The combined organics were washed with brine, dried with MgSO4, filtered, and concentrated to give N-(4-hydroxymethylphenyl)pyrid-3-ylmethylamine (88.2 g, 95% Yield).

Workup

  1. customThe layers were separated
  2. extractionthe aqueous extracted with EtOAc
  3. washThe combined organics were washed with brine
  4. dry with materialdried with MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-059e5d686f1945ddad0c8299e1c0baee
Source dataset
uspto-grants-2004_10
Patent number
US06800651B2

Reaction notes

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