Methanol → HCID 67983676, compound

HRID 1748162Notes

Reaction equation

CO.[CH:3]1([C:6]2[O:10][N:9]=[C:8]([CH:11]3[CH2:13][CH:12]3[C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=3)[C:7]=2[C:20](O)=[O:21])[CH2:5][CH2:4]1.[H-].[Al+3].[Li+].[H-].[H-].[H-]>C1COCC1>[CH:3]1([C:6]2[O:10][N:9]=[C:8]([CH:11]3[CH2:13][CH:12]3[C:14]3[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=3)[C:7]=2[CH2:20][OH:21])[CH2:5][CH2:4]1

Participants

Conditions

Temperature: 0 °C

Procedure

(5-cyclopropyl-3-2-phenylcyclopropyl)isoxazol-4-yl)methanol (rac-I-6F). To a solution of 5-cyclopropyl-3-(2-phenylcyclopropyl)isoxazole-4-carboxylic acid rac-I-6E (0.49 g, 1.82 mmol) in THF and cooled to 0°C. lithium aluminum hydride (4.5 mL, of a 1M solution in THF) was added dropwise. After stirring fo(12 h at rt, the reaction mixture was cooled back to 0°C. and quenched by dropwise addition of H2O (0.5 mL), 15% NaOH (0.5 mL), H2O (1 mL) followed by Na2SO4 and filtered through CELITE® under vacuum. The crude was purified by column chromatography on silica gel with DCM-EtOAc 0 to 5% gradient as eluent to give (5-cyclopropyl-3-(2-phenylcyclopropyl)isoxazol-4-yl)methanol. 1H NMR (400 MHz, DMSO) δ 7.31-727 (m, 2H), 7.21-7.17 (m, 3H), 5.00 (t, J=5.2 Hz, 1H), 4.42-4.33 (m, 2H), 2.39-2.35 (m, 1H), 2.23-2.13 (m, 2H), 1.57-1.52 (m, 1H), 1.46-1.42 (m, 1H), 1.05-1.04 (m, 2H), 0.95-0.91 (M, 2H). MS m/z 256.1 (M+1).

Workup

custom12 h
customat rt
customquenched by dropwise addition of H2O (0.5 mL), 15% NaOH (0.5 mL), H2O (1 mL)
filtrationfiltered through CELITE® under vacuum
customThe crude was purified by column chromatography on silica gel with DCM-EtOAc 0 to 5% gradient as eluent

Sources & evidence

ORD record: ord-0b926365ac8343989cd9ee378078093e
Source dataset: uspto-grants-2015_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09150568B2

Reaction notes

Loading…