Aminoacetaldehyde dimethyl acetal → (4,6-Difluoroindan-1-yl)-(2,2-dimethoxyethyl)amine

HRID 1735879Notes

Reaction equation

HRID 1735879 reaction equation
[F:1][C:2]1[CH:10]=[C:9]([F:11])[CH:8]=[C:7]2[C:3]=1[CH2:4][CH2:5][C:6]2=O.[CH3:13][O:14][CH:15]([O:18][CH3:19])[CH2:16][NH2:17].C([BH3-])#N.[Na+]>CO>[F:1][C:2]1[CH:10]=[C:9]([F:11])[CH:8]=[C:7]2[C:3]=1[CH2:4][CH2:5][CH:6]2[NH:17][CH2:16][CH:15]([O:18][CH3:19])[O:14][CH3:13]

Participants

5

Reactant 3

HCID 89728Aminoacetaldehyde dimethyl acetalHCID 5003444Sodium cyanoborohydride2×HCID 109539204,6-difluoro-2,3-dihydro-1H-inden-1-one

Product 1

HCID 19699493(4,6-Difluoroindan-1-yl)-(2,2-dimethoxyethyl)amine

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
65 °C

Procedure

A mixture of 4,6-difluoroindan-1-one (11.3 g, 67.26 mmol), 2,2-dimethoxyethylamine (7.07 g, 67.26 mmol) and sodium cyanoborohydride (4.23 g) in 75 mL of methanol was heated at gentle reflux and stirred under nitrogen for approximately 18 hours. Additional sodium cyanoborohydride (2.12 g) was added and the mixture was heated at 65° C. for 20 hours. The solvents were removed by evaporation. Purification of the residue by column chromatography on silica gel (elution: 2.5% methanol/methylene chloride) gave (4,6-difluoroindan-1-yl)-(2,2-dimethoxyethyl)amine.

Workup

  1. temperaturewas heated
  2. temperatureat gentle reflux
  3. customThe solvents were removed by evaporation
  4. customPurification of the residue by column chromatography on silica gel (elution: 2.5% methanol/methylene chloride)

Sources & evidence

ORD record
ord-96eec2ba525c4e409550013e22fe33c5
Source dataset
uspto-grants-1996_07
Patent number
US05538988

Reaction notes

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