Acetic Acid → HCID 69202633, compound

HRID 2377233Notes

Reaction equation

HRID 2377233 reaction equation
[C:1]12([O:14][CH2:13][CH2:12][O:11]1)[C:9]1[CH:8]=[CH:7][CH:6]=[C:5](N)[C:4]=1[CH2:3][CH2:2]2.[C:15](O)(=O)C.C=O.[C:21]([BH3-])#[N:22].[Na+]>CN(C)C=O>[CH3:15][N:22]([CH3:21])[C:5]1[C:4]2[CH2:3][CH2:2][C:1]3([O:14][CH2:13][CH2:12][O:11]3)[C:9]=2[CH:8]=[CH:7][CH:6]=1

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 712FormaldehydeHCID 5003444Sodium cyanoborohydrideHCID 69201851HCID 69201851, compound

Product 1

HCID 69202633HCID 69202633, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of Example 25 (100 mg, 0.52 mmol) in N,N-dimethylformamide (1 mL) was added acetic acid (0.1 mL) and a 37% aqueous solution of formaldehyde (0.5 mL, 5.23 mmol) and the mixture was stirred at room temperature for about 1 hour. Then sodium cyanoborohydride (330 mg, 5.23 mmol) was added and stirring at room temperature was continued overnight. The reaction was quenched by addition of saturated aqueous sodium bicarbonate and the mixture was extracted with dichloromethane. The combined organic extracts were dried (MgSO4), filtered, and concentrated under vacuum to provide the desired product. MS (ESI): m/z 220 (M+H)+.

Workup

  1. customThe reaction was quenched by addition of saturated aqueous sodium bicarbonate
  2. extractionthe mixture was extracted with dichloromethane
  3. dry with materialThe combined organic extracts were dried (MgSO4)
  4. filtrationfiltered
  5. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-2d3c2a0ba24642b3a2e2f1ebc4bef6da
Source dataset
uspto-grants-2008_12
Patent number
US07468371B2

Reaction notes

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