Water → HCID 19420919, compound

HRID 864039Notes

Reaction equation

HRID 864039 reaction equation
OC=[C:3]1[C:11]([CH3:13])([CH3:12])[C:10]2[C:5](=C[C:7](C)=[CH:8][CH:9]=2)[C:4]1=O.[NH:16]([CH2:18][CH:19](O)[CH3:20])[NH2:17].[OH2:22].[C:23]1(C)[CH:28]=CC=C[CH:24]=1>C1(C)C=CC(S(O)(=O)=O)=CC=1>[CH3:13][C:11]1([CH3:12])[C:3]2[C:20]([CH:19]=[C:18]3[C:4]=2[CH:5]=[N:17][N:16]3[CH2:24][CH:23]([OH:22])[CH3:28])=[C:8]([CH3:7])[CH:9]=[CH:10]1

Participants

6

Reactant 4

HCID 962WaterHCID 1140TolueneHCID 2361671-Hydrazinylpropan-2-olHCID 701855852-Hydroxymethylene-3,3,6-trimethyl-1-indanone

Product 1

HCID 19420919HCID 19420919, compoundYield 84%

Reagents, catalysts & solvents 1

HCID 6101p-Toluenesulfonic acidCatalyst

Procedure

A solution of 1.5 g (7.4 mmol) of 2-hydroxymethylene-3,3,6-trimethyl-1-indanone, 0.55 g (6.1 mmol) of (RS)-1-hydrazino-2-propanol and 100 mg of p-toluenesulfonic acid in 100 ml of anhydrous toluene was heated on a water separator for 2 hours. After concentration in a vacuum, the reaction mixture was purified by column chromatography on silica gel (ethyl acetate/hexane 4:1). 1.6 g (84%) of (RS)-1-(4,4,7-trimethyl-1,4-dihydro-indeno[2,1-c]-pyrazol-1-yl)-propan-2-ol were obtained as a yellow oil which was used directly in the next reaction.

Workup

  1. concentrationAfter concentration in a vacuum
  2. customthe reaction mixture was purified by column chromatography on silica gel (ethyl acetate/hexane 4:1)

Sources & evidence

ORD record
ord-092df8deb4274a89be91ffd944ff3372
Source dataset
uspto-grants-1996_10
Patent number
US05561150

Reaction notes

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