Diisobutylaluminum hydride → HCID 23499479, compound

HRID 411511Notes

Reaction equation

[F:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[CH2:9][CH2:10][N:11]1[CH2:16][CH2:15][CH:14]([S:17]([C:20]2[CH:25]=[CH:24][C:23]([C:26](OC)=[O:27])=[CH:22][CH:21]=2)(=[O:19])=[O:18])[CH2:13][CH2:12]1.CC(C[AlH]CC(C)C)C>C(Cl)Cl>[F:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[CH2:9][CH2:10][N:11]1[CH2:16][CH2:15][CH:14]([S:17]([C:20]2[CH:21]=[CH:22][C:23]([CH2:26][OH:27])=[CH:24][CH:25]=2)(=[O:18])=[O:19])[CH2:13][CH2:12]1

Participants

Conditions

Temperature: -78 °C

Procedure

1-(2-(2,4-Difluorophenyl)ethyl]-4-(4-methoxycarbonylphenylsulphonyl)piperidine (0.6 g, 1.42 mmol) was dissolved in anhydrous CH2Cl2 (15 ml) and stirred under nitrogen at −78° C. DIBAL-H (1M in THF, 4.25 ml, 4.25 mmol) was added dropwise. The reaction mixture was stirred at −78° C. for 15 min, allowed to warm up to room temperature and stirred for 1 h. Crushed Na2SO4.10H2O (5 eq.) was added and the mixture left at room temperature overnight. Inorganic solid was filtered off and washed with CH2Cl2 and EtOAc. The organic filtrate was concentrated to give a beige solid. δH (360 MHz, CDCl3) 1.64-1.77 (2H, m), 1.94-2.06 (4H, m), 2.47-2.55 (2H, m), 2.70-2.76 (2H, m), 2.83-2.94 (2H, m), 3.02-3.08 (2H, m), 4.82 (2H, s), 6.71-6.82 (2H, m), 7.06-7.14 (1H, m), 7.55 (2H, d, 8 Hz), 7.85 (2H, d, 8 Hz).

Workup

stirringThe reaction mixture was stirred at −78° C. for 15 min
temperatureto warm up to room temperature
stirringstirred for 1 h
filtrationInorganic solid was filtered off
washwashed with CH2Cl2 and EtOAc
concentrationThe organic filtrate was concentrated
customto give a beige solid

Sources & evidence

ORD record: ord-53335cde408e4fd58048eaa24157201d
Source dataset: uspto-grants-2003_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06559166B1

Reaction notes

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