Water → HCID 14126784, compound

HRID 477474Notes

Reaction equation

HRID 477474 reaction equation
[NH:1]1[CH2:5][CH2:4][CH2:3][CH2:2]1.O.[Cl-].[Na+].[OH-].[Na+].[O:11]1[CH:20]2[CH:12]1[CH2:13][C:14]1[C:19]2=[CH:18][CH:17]=[CH:16][CH:15]=1>CCOCC>[N:1]1([C@@H:13]2[C:14]3[C:19](=[CH:18][CH:17]=[CH:16][CH:15]=3)[CH2:20][C@H:12]2[OH:11])[CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

7

Reactant 5

HCID 962Water2×HCID 5234Sodium ChlorideHCID 14798Sodium HydroxideHCID 31268PyrrolidineHCID 92838Indene oxide

Product 1

HCID 14126784HCID 14126784, compound

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Conditions

Temperature
65 °C

Procedure

A solution of 10.8 ml of pyrrolidine in 6.75 g of 2,3-epoxy-indane [described by Mousseron et al., Bull. de Soc. Chim. de France, 1946, p. 629-630] was slowly added to 10.8 ml of demineralized water and after increasing the temperature to 65° C., the mixture was stirred for 90 minutes at 65° C. 20 ml of demineralized water were then added and excess pyrrolidine was distilled off at reduced pressure to obtain an oil phase and an aqueous phase. The aqueouse phase was saturated with sodium chloride and 1 ml of 32% sodium hydroxide was added thereto. The mixture was extacted with ether and the ether phase was dried and evaporated to dryness under reduced pressure. The oil residue was chromatographed over silica and eluted with ethyl acetate containing 5% of triethylamine to obtain 8.81 g of trans (±) 2,3-dihydro-1-(pyrrolidin-1-yl)-1H-inden-2-ol.

Workup

  1. distillationexcess pyrrolidine was distilled off at reduced pressure
  2. customto obtain an oil phase
  3. additionwas added
  4. dry with materialthe ether phase was dried
  5. customevaporated to dryness under reduced pressure
  6. customThe oil residue was chromatographed over silica
  7. washeluted with ethyl acetate containing 5% of triethylamine

Sources & evidence

ORD record
ord-32316cee98584da7a6044fcbc462067b
Source dataset
uspto-grants-1989_12
Patent number
US04888355

Reaction notes

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