Water → (R)-1-(7-methoxy-1,4-dihydro-indeno[2,1-c]pyrazol-1-yl)-propan-2-ol

HRID 864032Notes

Reaction equation

HRID 864032 reaction equation
[OH:1][CH:2]=C1CC2C(=CC(OC)=CC=2)C1=O.[NH:15]([CH2:17][C@H:18]([OH:20])[CH3:19])[NH2:16].[C:21]1([CH3:31])[CH:26]=[CH:25][C:24](S(O)(=O)=O)=[CH:23][CH:22]=1.O.[C:33]1([CH3:39])C=CC=C[CH:34]=1>>[CH3:2][O:1][C:22]1[CH:23]=[CH:24][CH2:25][C:26]2[C:21]=1[CH:31]=[C:39]1[C:33]=2[CH:34]=[N:16][N:15]1[CH2:17][C@H:18]([OH:20])[CH3:19]

Participants

6

Reactant 5

HCID 962WaterHCID 1140TolueneHCID 6101p-Toluenesulfonic acidHCID 28082612(R)-1-hydrazino-2-propanolHCID 69199600HCID 69199600, compound

Product 1

HCID 86749881(R)-1-(7-methoxy-1,4-dihydro-indeno[2,1-c]pyrazol-1-yl)-propan-2-olYield 68%

Procedure

A solution of 1.5 g (7.9 mmol) of 2-hydroxymethylene-6-methoxy-1-indanone, 0.78 g (8.6 mmol) of (R)-1-hydrazino-2-propanol and 100 mg of p-toluenesulfonic acid in 100 ml of anhydrous toluene was heated on a water separator for 1.5 hours. After concentration in a vacuum, the reaction mixture was purified by column chromatography on silica gel (ethyl acetate/hexane 4:1). 1.3 g (68%) of (R)-1-(7-methoxy-1,4-dihydro-indeno[2,1-c]pyrazol-1-yl)-propan-2-ol were obtained as a yellow solid 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-87b0ac227e8041d38eddbeb285f8ad6d
Source dataset
uspto-grants-1996_10
Patent number
US05561150

Reaction notes

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