Acetaldehyde → HCID 52950738, compound

HRID 1027581Notes

Reaction equation

F[C:2](F)(F)[C:3](O)=O.[Cl:8][C:9]1[CH:10]=[C:11]([C:16]2([C:36]([F:39])([F:38])[F:37])[O:20][N:19]=[C:18]([C:21]3[CH:34]=[CH:33][C:24]([C:25]([NH:27][CH:28]4[CH2:32][O:31][NH:30][CH2:29]4)=[O:26])=[C:23]([CH3:35])[CH:22]=3)[CH2:17]2)[CH:12]=[C:13]([Cl:15])[CH:14]=1.C(=O)C.[BH3-]C#N.[Na+]>CO>[Cl:15][C:13]1[CH:12]=[C:11]([C:16]2([C:36]([F:37])([F:39])[F:38])[O:20][N:19]=[C:18]([C:21]3[CH:34]=[CH:33][C:24]([C:25]([NH:27][CH:28]4[CH2:32][O:31][N:30]([CH2:2][CH3:3])[CH2:29]4)=[O:26])=[C:23]([CH3:35])[CH:22]=3)[CH2:17]2)[CH:10]=[C:9]([Cl:8])[CH:14]=1

Participants

Conditions

Temperature: 0 °C

Procedure

Crude 4-[5-(3,5-Dichloro-phenyl)-5-trifluoromethyl-4,5-dihydro-isoxazol-3-yl]-N-isoxazolidin-4-yl-2-methyl-benzamide trifluoroacetic acid salt (0.16 mmol) was dissolved in MeOH (0.8 ml). Then acetaldehyde (0.090 ml, 10 equiv) was added at 0° C. under an argon atmosphere. After stirring for 1 hour at 0° C., NaBH3CN (20 mg, 2 equiv) was added. The reaction mixture was left to stir over the weekend. It was then evaporated. Flash column chromatography eluting with ethyl acetate/methanol (10/0 to 9/1) afforded 7.5 mg of the expected compound as a mixture of diastereomers. LCMS (Method E) 2.02 min, M+H 516/518. 1H-NMR (MeOD, 400 MHz): 7.70-7.53 (m, 5H), 7.52-7.37 (m, 1H), 4.92-4.85 (m, 1H), 4.40-4.22 (m, 2H), 4.00 (d, 1H), 3.83-3.62 (m, 1H), 3.29-2.52 (m, 4H), 2.43 (s, 3H), 1.16 (t, 3H).

Workup

waitThe reaction mixture was left
stirringto stir over the weekend
customIt was then evaporated
washFlash column chromatography eluting with ethyl acetate/methanol (10/0 to 9/1)

Sources & evidence

ORD record: ord-95109b8f052b4b40bf316c412f875cbb
Source dataset: uspto-grants-2014_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08735362B2

Reaction notes

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