Formaldehyde → HCID 58042764, compound

HRID 564190Notes

Reaction equation

HRID 564190 reaction equation
[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][N:12]([CH2:15][CH2:16][C:17]2[CH:18]=[C:19]3[C:24](=[CH:25][CH:26]=2)[CH2:23][NH:22][CH2:21][CH2:20]3)[C:11](=[O:27])[CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C=O.[C:30](O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].C([O-])([O-])=O.[Na+].[Na+]>C1COCC1.C(O)(=O)C>[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][N:12]([CH2:15][CH2:16][C:17]2[CH:18]=[C:19]3[C:24](=[CH:25][CH:26]=2)[CH2:23][N:22]([CH3:30])[CH2:21][CH2:20]3)[C:11](=[O:27])[CH:10]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

7

Reactant 4

HCID 712FormaldehydeHCID 10340Sodium CarbonateHCID 5049666Sodium triacetoxyborohydrideHCID 58042745HCID 58042745, compound

Product 1

HCID 58042764HCID 58042764, compound

Reagents, catalysts & solvents 2

HCID 176Acetic AcidCatalystHCID 8028TetrahydrofuranSolvent

Procedure

To 170 mg (0.47 mmol) 4-benzyloxy-1-[2-(1,2,3,4-tetrahydro-isoquinolin-6-yl)-ethyl]-1H-pyridin-2-one (example 27.2) in 5.0 mL THF is added 57 μL (0.71 mmol) aqueous 37% formaldehyde solution. The mixture is acidified with 3 drops of acetic acid and then 150 mg (0.71 mmol) sodium triacetoxy-borohydride is added. The reaction mixture is stirred 2 h at RT, poured into aqueous 10% Na2CO3-solution and the layers are separated. The aqueous phase is extracted with tert-butylmethylether, the combined organic phase is washed a few times with water, dried over MgSO4, filtered and the solvent is evaporated to afford the product.

Workup

  1. customthe layers are separated
  2. extractionThe aqueous phase is extracted with tert-butylmethylether
  3. washthe combined organic phase is washed a few times with water
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. customthe solvent is evaporated
  7. customto afford the product

Sources & evidence

ORD record
ord-6e073b9ebd8b479483f9aeb2129e9a5e
Source dataset
uspto-grants-2011_11
Patent number
US08067590B2

Reaction notes

Loading…