Acetic Acid → HCID 58042693, compound

HRID 564174Notes

Reaction equation

HRID 564174 reaction equation
[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][N:12]([CH2:15][CH2:16][C:17]2[CH:27]=[CH:26][C:20]3[CH2:21][CH2:22][NH:23][CH2:24][CH2:25][C:19]=3[CH:18]=2)[C:11](=[O:28])[CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C=O.[C:31](O)(=O)C.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>C1COCC1.C([O-])(O)=O.[Na+]>[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][N:12]([CH2:15][CH2:16][C:17]2[CH:27]=[CH:26][C:20]3[CH2:21][CH2:22][N:23]([CH3:31])[CH2:24][CH2:25][C:19]=3[CH:18]=2)[C:11](=[O:28])[CH:10]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

7

Reactant 4

HCID 176Acetic AcidHCID 712FormaldehydeHCID 5049666Sodium triacetoxyborohydrideHCID 58042862HCID 58042862, compound

Product 1

HCID 58042693HCID 58042693, compound

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 516892Sodium BicarbonateSolvent

Procedure

To 100 mg (0.27 mmol) 4-benzyloxy-1-[2-(2,3,4,5-tetrahydro-1H-3-benzazepin-7-yl)-ethyl]-1H-pyridin-2-one (preparation 23.2) in 5.0 mL THF is added 43 μL (0.53 mmol) aqueous 37% formaldehyde solution. The mixture is acidified with acetic acid and then 62 mg (0.29 mmol) sodium triacetoxy-borohydride is added. The reaction mixture is stirred 3 h at RT and is diluted with aqueous saturated NaHCO3-solution. The mixture is stirred additional 1 h at RT, the layers are separated and the aqueous phase is extracted three times with DCM/MeOH. The combined organic phase is dried over MgSO4, filtered and the solvent is evaporated to afford the product.

Workup

  1. stirringThe mixture is stirred additional 1 h at RT
  2. customthe layers are separated
  3. extractionthe aqueous phase is extracted three times with DCM/MeOH
  4. dry with materialThe combined organic phase is dried over MgSO4
  5. filtrationfiltered
  6. customthe solvent is evaporated
  7. customto afford the product

Sources & evidence

ORD record
ord-9580bd2519ba4a11913ddffef96e0e3f
Source dataset
uspto-grants-2011_11
Patent number
US08067590B2

Reaction notes

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