Potassium Hydroxide → HCID 21221833, compound

HRID 1585168Notes

Reaction equation

HRID 1585168 reaction equation
[OH-].[K+].FC(F)(F)C([NH:7][CH:8]1[CH2:16][C:15]2[C:10](=[CH:11][C:12]([CH2:22][O:23]C(=O)C)=[C:13]([CH2:17][O:18]C(=O)C)[CH:14]=2)[CH2:9]1)=O>O.CO>[NH2:7][CH:8]1[CH2:9][C:10]2[C:15](=[CH:14][C:13]([CH2:17][OH:18])=[C:12]([CH2:22][OH:23])[CH:11]=2)[CH2:16]1

Participants

5

Reactant 2

HCID 14797Potassium HydroxideHCID 21221815HCID 21221815, compound

Product 1

HCID 21221833HCID 21221833, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

A solution of potassium hydroxide (10.10 g, 0.180 mol) in water (35 ml) was added to a solution of 2-(trifluoroacetylamino)-5,6-bis(acetoxymethyl)indane 47 (20.1 g, 53.8 mmol) in methanol (200 ml) at room temperature, and the mixture was heated to reflux for 2.5 hours. The solvent was removed under vacuum to leave 2-amino-5,6-bis(hydroxymethyl)indane (48) as a semisolid. The crude product was mixed with 1-bromopropane (27.1 g, 0.220 mol) and potassium carbonate (22.32 g, 0.162 mol) in acetonitrile (100 ml), and the mixture was stirred mechanically at reflux on the steam bath for 17 hours. 1-Bromopropane (6.8 g, 0.055 mol) was added, and the reflux was continued for 4 hours. The mixture was diluted with water and extracted twice with ethyl acetate. The extracts were washed with brine and dried (MgSO4). The solvent was removed under vacuum to leave a brown oil (15.75 g). Purification by flash chromatography (230-400 mesh silica gel, ethyl acetate to 30% tetrahydrofuran in ethyl acetate) gave the title compound (49) as a solid (12.1 g, 81%). A sample (0.50 g) was crystallized from ethyl acetate/hexane to give white crystals (0.48 g).

Workup

  1. temperaturethe mixture was heated
  2. temperatureto reflux for 2.5 hours
  3. customThe solvent was removed under vacuum

Sources & evidence

ORD record
ord-ff3c21afb0a742e683abffdeecc5db57
Source dataset
uspto-grants-1999_08
Patent number
US05936000

Reaction notes

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