HCID 20585422, compound → HCID 22258933, compound

HRID 412269Notes

Reaction equation

HRID 412269 reaction equation
[NH2:1][C:2]1[C:7]([C:8](OC(C)(C)C)=[O:9])=[C:6]([C:15]2[CH2:16][N:17]([C:21]([O:23][C:24]([CH3:27])([CH3:26])[CH3:25])=[O:22])[CH2:18][CH2:19][CH:20]=2)[CH:5]=[C:4]([C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][C:29]=2[O:34][CH2:35][C:36]2[CH:41]=[CH:40][C:39]([O:42][CH3:43])=[CH:38][CH:37]=2)[N:3]=1.[H-].COCCO[Al+]OCCOC.[Na+].[H-]>C1COCC1>[NH2:1][C:2]1[C:7]([CH2:8][OH:9])=[C:6]([C:15]2[CH2:16][N:17]([C:21]([O:23][C:24]([CH3:27])([CH3:26])[CH3:25])=[O:22])[CH2:18][CH2:19][CH:20]=2)[CH:5]=[C:4]([C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][C:29]=2[O:34][CH2:35][C:36]2[CH:37]=[CH:38][C:39]([O:42][CH3:43])=[CH:40][CH:41]=2)[N:3]=1

Participants

4

Reactant 2

HCID 20585422HCID 20585422, compoundHCID 21584525Sodium bis(2-methoxyethoxy)aluminiumhydride

Product 1

HCID 22258933HCID 22258933, compoundYield 57%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

To a cooled (0° C.) solution of di(tert-butyl) 2′-amino-6′-{2-[(4-methoxybenzyl)oxy]phenyl}-5,6-dihydro-3,4′-bipyridine-1,3′(2H)-dicarboxylate (50.0 mg, 0.09 mmol) in THF (4.5 mL) was added sodium bis(2-methoxyethoxy)aluminum hydride (0.10 mL) dropwise, then stirred for 1 hr at 0° C. The reaction was quenched by an addition of saturated NH4Cl solution, filtered, and washed with ethyl acetate. The combined organic phase was washed with brine, dried over MgSO4, filtered and evaporated. The crude product was purified by preparative silica gel TLC (15% acetone in chloroform) to give tert-butyl 2′-amino-3′-(hydroxymethyl)-6′-{2-[(4-methoxybenzyl)oxy]phenyl}-5,6-dihydro-3,4′-bipyridine-1(2H)-carboxylate as a white foam (25 mg, yield 57%).

Workup

  1. customThe reaction was quenched by an addition of saturated NH4Cl solution
  2. filtrationfiltered
  3. washwashed with ethyl acetate
  4. washThe combined organic phase was washed with brine
  5. dry with materialdried over MgSO4
  6. filtrationfiltered
  7. customevaporated
  8. customThe crude product was purified by preparative silica gel TLC (15% acetone in chloroform)

Sources & evidence

ORD record
ord-f6c20315f10346e1ae0dba0fd74c6d64
Source dataset
uspto-grants-2003_05
Patent number
US06562811B1

Reaction notes

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