Formaldehyde → HCID 10927161, compound

HRID 1976769Notes

Reaction equation

HRID 1976769 reaction equation
[OH:1][CH:2]([C:16]1[CH:21]=[C:20]([O:22][CH3:23])[C:19]([O:24][CH3:25])=[C:18]([O:26][CH3:27])[CH:17]=1)[CH2:3][NH:4][C:5]([C:7]1[CH:8]=[C:9]2[C:13](=[CH:14][CH:15]=1)[NH:12][CH:11]=[CH:10]2)=[O:6].C=O.[C:30]([BH3-])#N.[Na+]>C(O)(=O)C>[OH:1][CH:2]([C:16]1[CH:21]=[C:20]([O:22][CH3:23])[C:19]([O:24][CH3:25])=[C:18]([O:26][CH3:27])[CH:17]=1)[CH2:3][NH:4][C:5]([C:7]1[CH:8]=[C:9]2[C:13](=[CH:14][CH:15]=1)[N:12]([CH3:30])[CH2:11][CH2:10]2)=[O:6]

Participants

5

Reactant 3

HCID 712FormaldehydeHCID 5003444Sodium cyanoborohydrideHCID 11810774HCID 11810774, compound

Product 1

HCID 10927161HCID 10927161, compoundYield 100.7%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A suspension of indole-5-carboxylic acid, (N-[2-hydroxy-2-(3,4,5-trimethoxyphenyl)ethyl]) amide (207 mg, 0.56 mmol) and paraformaldehyde (168 mg, 5.6 mmol) in acetic acid (5 mL) was treated with sodium cyanoborohydride (176 mg, 2.79 mmol), stirred for 18 hours, and concentrated. The concentrate was partitioned between ethyl acetate and 10% NaHCO3, washed sequentially with 10% NaHCO3 and brine, dried (MgSO4), filtered, and concentrated to provide 218 mg of the desired product. MS (ESI(+)) m/z 387 (M+H)+;

Workup

  1. concentrationconcentrated
  2. customThe concentrate was partitioned between ethyl acetate and 10% NaHCO3
  3. washwashed sequentially with 10% NaHCO3 and brine
  4. dry with materialdried (MgSO4)
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-227e7132fe244bf9822ffe7b39ab0894
Source dataset
uspto-grants-2001_05
Patent number
US06228868B1

Reaction notes

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