Ammonium Acetate → HCID 19801049, compound

HRID 1646658Notes

Reaction equation

HRID 1646658 reaction equation
[O:1]1[CH:3]([CH2:4][CH:5]=[C:6]([CH3:8])[CH3:7])[C:2]1([CH:10]1[CH:15]([O:16][CH3:17])[C:14](=O)[CH2:13][CH2:12][C:11]1([CH2:20][S:21][CH2:22][C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][C:24]=1[CH2:29][OH:30])[OH:19])[CH3:9].C([O-])(=O)C.[NH4+].C([BH3-])#[N:37].[Na+]>CO>[NH2:37][CH:14]1[CH2:13][CH2:12][C:11]([CH2:20][S:21][CH2:22][C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][C:24]=2[CH2:29][OH:30])([OH:19])[CH:10]([C:2]2([CH3:9])[O:1][CH:3]2[CH2:4][CH:5]=[C:6]([CH3:8])[CH3:7])[CH:15]1[O:16][CH3:17]

Participants

5

Reactant 3

HCID 517165Ammonium AcetateHCID 5003444Sodium cyanoborohydrideHCID 19801074HCID 19801074, compound

Product 1

HCID 19801049HCID 19801049, compoundYield 58.6%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

2-(1,2-Epoxy-1,5-dimethyl-4-hexenyl)-1-(2-hydroxymethylbenzyl)thiomethyl-3-methoxy-4oxocyclohexanol (1.07 g) and ammonium acetate (1.86 g) were dissolved in methanol (25 ml). To the solution was added sodium cyanoborohydride (304 mg), and the mixture was stirred for one hour. The solvent was distilled off under reduced pressure, and the residue was dissolved in ethyl acetate (100 ml). The solution was washed with a saturated aqueous solution of sodium hydrogencarbonate and a saturated aqueous solution of sodium chloride, followed by drying over anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure, and the residue was purified by means of a silica gel column chromatography (carrier 40 g, developing solvent: chloroform-methanol-NH4OH=20:1:0.1) to obtain 4-amino-2-(1,2-epoxy-1,5-dimethyl-4-hexenyl)-1-(2-hydroxymethylbenzyl)thiomethyl-3-methoxycyclohexanol (629 mg; yield 58%) as a colorless oily product.

Workup

  1. distillationThe solvent was distilled off under reduced pressure
  2. dissolutionthe residue was dissolved in ethyl acetate (100 ml)
  3. washThe solution was washed with a saturated aqueous solution of sodium hydrogencarbonate
  4. dry with materialby drying over anhydrous magnesium sulfate
  5. distillationThe solvent was distilled off under reduced pressure
  6. customthe residue was purified by means of a silica gel column chromatography (carrier 40 g, developing solvent: chloroform-methanol-NH4OH=20:1:0.1)

Sources & evidence

ORD record
ord-a2b635cff3ec4b1d8ebd26bb4e7890e0
Source dataset
uspto-grants-1993_01
Patent number
US05180735

Reaction notes

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