Diisobutylaluminumhydride → 1-(3,5-Bis-trifluoromethyl-benzyl)-5-morpholin-4-yl-1h-[1,2,3]triazole-4-carbaldehyde

HRID 2251981Notes

Reaction equation

[F:1][C:2]([F:34])([F:33])[C:3]1[CH:4]=[C:5]([CH:26]=[C:27]([C:29]([F:32])([F:31])[F:30])[CH:28]=1)[CH2:6][N:7]1[C:11]([N:12]2[CH2:17][CH2:16][O:15][CH2:14][CH2:13]2)=[C:10]([C:18](N2CCOCC2)=[O:19])[N:9]=[N:8]1.[H-].C([Al+]CC(C)C)C(C)C>C1COCC1.C1(C)C=CC=CC=1>[F:32][C:29]([F:30])([F:31])[C:27]1[CH:26]=[C:5]([CH:4]=[C:3]([C:2]([F:1])([F:33])[F:34])[CH:28]=1)[CH2:6][N:7]1[C:11]([N:12]2[CH2:17][CH2:16][O:15][CH2:14][CH2:13]2)=[C:10]([CH:18]=[O:19])[N:9]=[N:8]1

Participants

Conditions

Temperature: -78 °C

Procedure

Dissolve [1-(3,5-bis-trifluoromethyl-benzyl)-5-morpholin-4-yl-1H-[1,2,3]triazol-4-yl]-morpholin-4-yl-methanone in THF. Cool to −78° C., slowly add 28.3 ml (4 eq) of 1M diisobutyl aluminum hydride in toluene, and stir 2.5 hours. Move to 0° C. ice bath and allow reaction to slowly warm while stirring overnight. Slowly quench by adding ˜5 ml 1N HCl while still at 0° C. then warming to RT. Pour into 50 ml 1N NaOH. Extract with EtOAc, then wash organic layer with 1N HCl. Concentrate organic layer to give the desired aldehyde, which can be used without further purification. MS (IS) 409.2 (M+1). Rf=0.61 (1:1 Hexanes:EtOAc)

Workup

customMove to 0° C.
customreaction
temperatureto slowly warm
customSlowly quench
additionby adding ˜5 ml 1N HCl while still at 0° C.
temperaturethen warming to RT
additionPour into 50 ml 1N NaOH
extractionExtract with EtOAc

Sources & evidence

ORD record: ord-3dbc0fb65c3a4801bef192d4de26caf6
Source dataset: uspto-grants-2008_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07320994B2

Reaction notes

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