Methanol → HCID 23453183, compound

HRID 1277687Notes

Reaction equation

HRID 1277687 reaction equation
Cl.Cl.[NH2:3][CH2:4][C:5]1([CH2:14][OH:15])[CH:10]([OH:11])[CH:9]([OH:12])[CH:8]([OH:13])[CH2:7][NH:6]1.CO.[C:18]1(=O)[CH2:29][CH2:28][CH2:27][CH2:26][CH2:25][CH2:24][CH2:23][CH2:22][CH2:21][CH2:20][CH2:19]1.C([BH3-])#N.[Na+]>O.C(O)(=O)C>[CH:18]1([NH:3][CH2:4][C:5]2([CH2:14][OH:15])[CH:10]([OH:11])[CH:9]([OH:12])[CH:8]([OH:13])[CH2:7][NH:6]2)[CH2:29][CH2:28][CH2:27][CH2:26][CH2:25][CH2:24][CH2:23][CH2:22][CH2:21][CH2:20][CH2:19]1

Participants

7

Reactant 4

HCID 887MethanolHCID 13246CyclododecanoneHCID 5003444Sodium cyanoborohydrideHCID 20449506HCID 20449506, compound

Product 1

HCID 23453183HCID 23453183, compoundYield 67%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 962WaterSolvent

Procedure

2.65 g of 2-aminomethyl-2-hydroxymethyl-3,4,5-trihydroxypiperidine dihydrochloride (Preparation example 11) are dissolved in 21 ml of water, and 60 ml of methanol 1.5 ml of acetic acid and 6 g of cyclododecanone are then added. When a solution is obtained, 1.35 g of sodium cyanoborohydride are added. The mixture is stirred for 18 hours and the product which has precipitated is filtered off and washed with water. 2.4 g of a colourless complex are obtained, and the complex is discharged onto an Amberlite IR 120 H+ exchange column to liberate the base. The column is washed with about 3 l of water and the desired compound is liberated with 2% strength aqueous ammonia. The product fractions, determined by thin layer chromatography, are collected and concentrated. The evaporation residue crystallises on trituration with isopropanol. 1.8 g of a colourless product of melting point 171°-172° C. are obtained.

Workup

  1. customWhen a solution is obtained
  2. customthe product which has precipitated
  3. filtrationis filtered off
  4. washwashed with water

Sources & evidence

ORD record
ord-e66e3d1b5c9548c3a629d160263eec33
Source dataset
uspto-grants-1981_07
Patent number
US04278683

Reaction notes

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