Diazomethane → HCID 19420935, compound

HRID 864049Notes

Reaction equation

HRID 864049 reaction equation
[N+](=[CH2:3])=[N-].[CH3:4][O:5][C:6]1[CH:17]=[CH:16][CH2:15][C:14]2[C:7]=1[CH:8]=[C:9]1[C:13]=2[C:12](=[O:18])[NH:11][N:10]1[CH2:19][CH:20]([OH:22])[CH3:21]>C(OCC)C.CO>[CH3:3][O:18][C:12]1[C:13]2[C:9](=[CH:8][C:7]3[C:14]=2[CH2:15][CH:16]=[CH:17][C:6]=3[O:5][CH3:4])[N:10]([CH2:19][CH:20]([OH:22])[CH3:21])[N:11]=1

Participants

5

Reactant 2

HCID 9550DiazomethaneHCID 19420911HCID 19420911, compound

Product 1

HCID 19420935HCID 19420935, compoundYield 81%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 3283Diethyl EtherSolvent2×

Procedure

A solution of 0.79 g (18.8 mmol) of diazomethane in 56 ml of anhydrous diethyl ether was added while stirring to a solution of 2.44 g (9.37 mmol) of (RS)-1-(7-methoxy-1,4-dihydro-indeno[2,1-c]pyrazol-3-on-1-yl)-propan-2-ol in 80 ml of anhydrous diethyl ether and 50 ml of anhydrous methanol. The mixture was stirred at room temperature for a further 15 hours and subsequently concentrated in a vacuum. 2.08 g (81%) of (RS)-1-(3,7-dimethoxy-1,4-dihydro-indeno[2,1-c]pyrazol-1-yl)-propan-2-ol were obtained as a brown solid which was used directly in the next reaction.

Workup

  1. concentrationsubsequently concentrated in a vacuum

Sources & evidence

ORD record
ord-e1aee0f0b98147ee98fa6af3728001d5
Source dataset
uspto-grants-1996_10
Patent number
US05561150

Reaction notes

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