Formaldehyde → HCID 10138875, compound

HRID 985160Notes

Reaction equation

HRID 985160 reaction equation
[C:1]([O:5][C:6](=[O:31])[NH:7][CH2:8][CH2:9][N:10]1[C:19]([CH2:20]N)=[C:18]([C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)[C:17]2[C:12](=[CH:13][CH:14]=[C:15]([O:28][CH3:29])[CH:16]=2)[C:11]1=[O:30])([CH3:4])([CH3:3])[CH3:2].[CH2:32]=O.[C:34]([BH3-])#[N:35].[Na+].CO>CCCCCC.CCOCC>[C:1]([O:5][C:6](=[O:31])[NH:7][CH2:8][CH2:9][N:10]1[C:19]([CH2:20][N:35]([CH3:34])[CH3:32])=[C:18]([C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)[C:17]2[C:12](=[CH:13][CH:14]=[C:15]([O:28][CH3:29])[CH:16]=2)[C:11]1=[O:30])([CH3:4])([CH3:3])[CH3:2]

Participants

6

Reactant 4

HCID 712FormaldehydeHCID 887MethanolHCID 5003444Sodium cyanoborohydrideHCID 20768296HCID 20768296, compound

Product 1

HCID 10138875HCID 10138875, compoundYield 76.2%

Reagents, catalysts & solvents 1

HCID 21584099Diethylether hexaneSolvent

Procedure

A solution of 114 (2.72 g, 6.43 mmol), formaldehyde (12.3M, 2.62 mL, 32.2 mmol), sodium cyanoborohydride (1.0M in tetrahydrofuran, 32.2 mL, 32.2 mmol), and methanol (100 mL) were heated at reflux for 1 h. The contents of the reaction flask were cooled and the solvent was removed in vacuo. Sat. sodium bicarbonate was added and the resulting mixture was extracted with ethyl acetate (3×). The combined organic extracts were dried with magnesium sulfate (anh.) and filtered. The filtrate was removed by rotary evaporation to give a colorless oil. Trituration with hexane:ether (1:1) gave 115 as a white solid (2.21 g, 4.90 mmol, 76.2%).

Workup

  1. temperatureat reflux for 1 h
  2. temperatureThe contents of the reaction flask were cooled
  3. customthe solvent was removed in vacuo
  4. additionSat. sodium bicarbonate was added
  5. extractionthe resulting mixture was extracted with ethyl acetate (3×)
  6. dry with materialThe combined organic extracts were dried with magnesium sulfate (anh.)
  7. filtrationfiltered
  8. customThe filtrate was removed by rotary evaporation
  9. customto give a colorless oil

Sources & evidence

ORD record
ord-d972bd7e5a404fb783145fd80dd0f174
Source dataset
uspto-grants-2005_03
Patent number
US06870055B2

Reaction notes

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