6-Aminohexanoic Acid → HCID 58636712, compound

HRID 1158947Notes

Reaction equation

HRID 1158947 reaction equation
[CH3:1][C:2]1[N:7]=[CH:6][C:5]([CH2:8][OH:9])=[C:4]([CH:10]=O)[C:3]=1[OH:12].[NH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][C:19]([OH:21])=[O:20].[BH4-].[Na+]>CO>[OH-:9].[NH4+:7].[OH:12][C:3]1[C:2]([CH3:1])=[N:7][CH:6]=[C:5]([CH2:8][OH:9])[C:4]=1[CH2:10][NH:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][C:19]([OH:21])=[O:20]

Participants

6

Reactant 3

HCID 5646-Aminohexanoic AcidHCID 1050PyridoxalHCID 4311764Sodium borohydride

Product 2

HCID 14923Ammonium HydroxideYield 30%HCID 58636712HCID 58636712, compoundYield 81.3%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

A mixture of pyridoxal (20.0 g, 98.5 mmol) and 6-aminocaproic acid (22.2 g, 169 mmol) was stirred in methyl alcohol (2 L) at room temperature for 12 hours. The solution was placed in an ice bath and sodium borohydride (5.7 g, 167 mmol) was added slowly. The resulting mixture was stirred for one hour at room temperature and then the solvent was evaporated to dryness. The crude product was purified by column chromatography on silica gel using a mixture of dichloromethane:methyl alcohol:30% ammonium hydroxide (5:5:1) to give 6-[(3-hydroxy-5-hydroxymethyl-2-methyl-pyridin-4-ylmethyl)-amino]hexanoic acid (40) (11.3 g, 41% yield) as colorless crystals.

Workup

  1. customThe solution was placed in an ice bath
  2. customthe solvent was evaporated to dryness
  3. customThe crude product was purified by column chromatography on silica gel using
  4. additiona mixture of dichloromethane

Sources & evidence

ORD record
ord-615c964f82dc4fdb9d48e60a082253f8
Source dataset
uspto-grants-2010_10
Patent number
US07812037B2

Reaction notes

Loading…