Methanol → [2-(2-Isopropyl-2H-[1,2,4]triazol-3-yl)-4,5-dihydro-6-oxa-3-thia-1-aza-benzo[e]azulen-8-yl]-methanol

HRID 1848998Notes

Reaction equation

C[O:2][C:3]([C:5]1[CH:26]=[CH:25][C:8]2[C:9]3[N:10]=[C:11]([C:17]4[N:18]([CH:22]([CH3:24])[CH3:23])[N:19]=[CH:20][N:21]=4)[S:12][C:13]=3[CH2:14][CH2:15][O:16][C:7]=2[CH:6]=1)=O.[H-].C([Al+]CC(C)C)C(C)C.CO.C(C(C(C([O-])=O)O)O)([O-])=O.[Na+].[K+]>C1COCC1>[CH:22]([N:18]1[C:17]([C:11]2[S:12][C:13]3[CH2:14][CH2:15][O:16][C:7]4[CH:6]=[C:5]([CH2:3][OH:2])[CH:26]=[CH:25][C:8]=4[C:9]=3[N:10]=2)=[N:21][CH:20]=[N:19]1)([CH3:24])[CH3:23]

Participants

Conditions

Temperature: 0 °C

Procedure

To a suspension of 2-(2-isopropyl-2H-[1,2,4]triazol-3-yl)-4,5-dihydro-6-oxa-3-thia-1-aza-benzo[e]azulene-8-carboxylic acid methyl ester (778 mg, 2.1 mmol) in THF (20 mL) at −78° C. under nitrogen was added dropwise diisobutyl aluminium hydride (1.5M in toluene, 4.2 mL, 6.3 mmol) and the reaction mixture was stirred at 0° C. for 2 hours. MeOH (10 mL) was added cautiously followed by an aqueous 1M potassium sodium tartrate solution (7 mL) at RT. The mixture was concentrated in vacuo to remove organic solvent and the aqueous phase was extracted with DCM (×3). The combined organic extracts were dried (MgSO4) and concentrated in vacuo to give the title compound as an off-white solid (713 mg, 99%). LCMS: RT=4.14 min, [M+H]+=343

Workup

concentrationThe mixture was concentrated in vacuo
customto remove organic solvent
extractionthe aqueous phase was extracted with DCM (×3)
dry with materialThe combined organic extracts were dried (MgSO4)
concentrationconcentrated in vacuo

Sources & evidence

ORD record: ord-4db4856b7cf14f31ae916aebffc5e8bb
Source dataset: uspto-grants-2015_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08952043B2

Reaction notes

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