Acetic Acid → HCID 23453192, compound

HRID 1277686Notes

Reaction equation

HRID 1277686 reaction equation
[C:1]([NH:9][CH2:10][C:11]1([CH2:20][OH:21])[CH:16]([OH:17])[CH:15]([OH:18])[CH:14]([OH:19])[CH2:13][NH:12]1)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C([BH3-])#N.[Na+].[C:26](O)(=O)[CH3:27]>CO.O>[CH2:1]([N:12]1[CH2:13][CH:14]([OH:19])[CH:15]([OH:18])[CH:16]([OH:17])[C:11]1([CH2:10][NH:9][C:1](=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1)[CH2:20][OH:21])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:26][CH3:27]

Participants

6

Reactant 3

HCID 176Acetic AcidHCID 5003444Sodium cyanoborohydrideHCID 23453189HCID 23453189, compound

Product 1

HCID 23453192HCID 23453192, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Conditions

Temperature
5 °C

Procedure

2.96 g of 2-benzoylaminomethyl-2-hydroxymethyl-3,4,5-trihydroxypiperidine (Example 3) are dissolved in a mixture of 40 ml of methanol, 2 ml of water and 2.7 ml of acetic acid, and 5.7 ml of nonylaldehyde are added. The solution is cooled to 5° C. in an ice-bath; 1.35 g of sodium cyanoborohydride are then added. The mixture is stirred for 30 minutes, whilst cooling, and then at room temperature for 24 hours. It is concentrated, the residue is dissolved in 30 ml of methanol/water 6:1 and the solution is discharged onto a column 30 cm long and 3 cm wide which is filled with Amberlite IR 120, H+ form. The column is washed thoroughly with methanol/water in the ratio 8:1 and then eluted with 0.2% strength ammonia in methanol/water 6:1. The pure fractions, determined by thin layer chromatography, are combined and concentrated. 2.6 g of an almost colourless oil are obtained.

Workup

  1. additionare added
  2. temperaturewhilst cooling
  3. waitat room temperature for 24 hours
  4. concentrationIt is concentrated
  5. dissolutionthe residue is dissolved in 30 ml of methanol/water 6:1
  6. addition3 cm wide which is filled with Amberlite IR 120, H+ form
  7. washThe column is washed thoroughly with methanol/water in the ratio 8:1
  8. washeluted with 0.2% strength ammonia in methanol/water 6:1
  9. concentrationconcentrated
  10. custom2.6 g of an almost colourless oil are obtained

Sources & evidence

ORD record
ord-5dc2691bb5ee40aaa899db06609ee603
Source dataset
uspto-grants-1981_07
Patent number
US04278683

Reaction notes

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