Diisobutylaluminum hydride → HCID 69156647, compound

HRID 1624299Notes

Reaction equation

C([O:4][CH2:5][CH2:6][C:7]([F:21])([F:20])[CH2:8][N:9]1[C:13](=[O:14])[C:12]2=[CH:15][CH:16]=[CH:17][CH:18]=[C:11]2[C:10]1=[O:19])(=O)C.CC(C[AlH]CC(C)C)C.[NH4+].[Cl-].[O-]S([O-])(=O)=O.[Mg+2]>C1COCC1.C(OCC)C>[F:21][C:7]([F:20])([CH2:6][CH2:5][OH:4])[CH2:8][N:9]1[C:13](=[O:14])[C:12]2=[CH:15][CH:16]=[CH:17][CH:18]=[C:11]2[C:10]1=[O:19]

Participants

Conditions

Temperature: -78 °C

Procedure

The above N-(4-acetoxy-2,2-difluorobutyl)phthalimide (3.84 g, 12.9 mmol) was dissolved in THF (65 mL) and cooled to −78° C. A solution of DIBAL-H (32.3 mL, 1.0 M in hexanes, 32.3 mmol) was added slowly and the solution allowed to stir 0.5 h. Saturated aqueous NH4Cl solution (15 mL) was then added and the solution was warmed to room temperature. MgSO4 (15 g) and diethyl ether (200 mL) were added, and the mixture was filtered through celite, washing with excess 1:1 Et2O/THE (1 L). The filtrate was then concentrated under reduced pressure and the crude material was purified by column chromatography on silica gel (1:2 EtOAc/hexanes) to give the desired N-(2,2-difluoro-4-hydroxybutyl)phthalimide as a pale yellow solid (1.47 g, 45%). 1H NMR (CDCl3) δ 1.97 (t, OH, J=6.0 Hz), 2.22 (tt, 2H, J=16.5, 6.0 Hz), 3.95 (q, 2H, J=6.0 Hz), 4.19 (t, 2H, J=15 Hz), 7.75 (m, 2H), 7.90 (m, 2H).

Workup

temperaturethe solution was warmed to room temperature
filtrationthe mixture was filtered through celite
washwashing with excess 1:1 Et2O/THE (1 L)
concentrationThe filtrate was then concentrated under reduced pressure
customthe crude material was purified by column chromatography on silica gel (1:2 EtOAc/hexanes)

Sources & evidence

ORD record: ord-4adbeee764d94d248d279fe8440a87c8
Source dataset: uspto-grants-2014_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08778967B2

Reaction notes

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