Lithium aluminum hydride → [5-(3-chloro-benzylamino)-2-methyl-2H-pyrazol-3-yl]-methanol

HRID 1952177Notes

Reaction equation

C[O:2][C:3]([C:5]1[N:6]([CH3:19])[N:7]=[C:8]([NH:10][CH2:11][C:12]2[CH:17]=[CH:16][CH:15]=[C:14]([Cl:18])[CH:13]=2)[CH:9]=1)=O.[AlH4-].[Li+].O.O.O.O.O.O.O.O.O.O.S([O-])([O-])(=O)=O.[Na+].[Na+]>O1CCCC1>[Cl:18][C:14]1[CH:13]=[C:12]([CH:17]=[CH:16][CH:15]=1)[CH2:11][NH:10][C:8]1[CH:9]=[C:5]([CH2:3][OH:2])[N:6]([CH3:19])[N:7]=1

Participants

Conditions

Temperature: -40 °C

Procedure

5-(3-Chloro-benzylamino)-2-methyl-2H-pyrazole-3-carboxylic acid methyl ester (646, 0.944 g, 3.37 mmol) was combined with tetrahydrofuran (20 mL) and the solution was cooled to −40° C. 1.0 M lithium tetrahydroaluminate in tetrahydrofuran (3.7 mL) was added and the reaction was stirred for 45 min at −20° C. 1.0 M lithium tetrahydroaluminate in tetrahydrofuran (3.7 mL) was added at −40° C. and the reaction was stirred to 10° C. Sodium sulfate decahydrate was added in small portions and the mixture was stirred for two hours at room temperature, then filtered through Celite and concentrated. The resulting compound (647, 0.821 g, 97%) was washed with a mixture of ethyl acetate:hexanes and dried under reduced pressure.

Workup

stirringthe reaction was stirred to 10° C
stirringthe mixture was stirred for two hours at room temperature
filtrationfiltered through Celite
concentrationconcentrated
washThe resulting compound (647, 0.821 g, 97%) was washed with a mixture of ethyl acetate
dry with materialhexanes and dried under reduced pressure

Sources & evidence

ORD record: ord-d35fbae0b42742f68d34ede9e0242081
Source dataset: uspto-grants-2013_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08404700B2

Reaction notes

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