Ammonium Chloride → 3,3-Dimethyl-1-[2-(2-phenethyl-4-phenyl-butyryl)-piperidin-1-yl]-butane-1,2-dione

HRID 1828064Notes

Reaction equation

C[O:2][C:3](=O)[C:4](=[O:30])[N:5]1[CH2:10][CH2:9][CH2:8][CH2:7][CH:6]1[C:11](=[O:29])[CH:12]([CH2:21][CH2:22][C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1)[CH2:13][CH2:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1.[CH3:32][C:33]([Mg]Cl)([CH3:36])[CH2:34]C.[Cl-].[NH4+]>C1COCC1>[CH3:32][C:33]([CH3:36])([CH3:34])[C:3](=[O:2])[C:4]([N:5]1[CH2:10][CH2:9][CH2:8][CH2:7][CH:6]1[C:11](=[O:29])[CH:12]([CH2:21][CH2:22][C:23]1[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=1)[CH2:13][CH2:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)=[O:30]

Participants

Conditions

Temperature: -78 °C

Procedure

To a solution of 0.38 g (0.90 mmol) of 5 in anhydrous THF (5 mL) was added dropwise at −78° C. a 1.0M solution of 1.9 mL (1.90 mmol) of 1,1-dimethylpropyl magnesium chloride in THF, and the mixture was stirred for 3 hours at −78° C. The solution was poured over saturated ammonium chloride (50 mL) and extracted with EtOAc (2×100 mL). The organic phase was dried (MgSO4) and evaporated to a clear oil which was subject to column chromatography (EtOAc/Hexanes, 1:4) to yield 0.31 g (74.5%) of 6 as a clear oil. TLC Rf=0.8 (EtOAc/Hexanes, 1:4) 1H NMR (CDCl3, 400 MHz): δ 0.94 (t, 3H, J=7.5 Hz); 1.24 (s, 3H); 1.28 (s, 3H); 1.42–2.06 (m, 11H); 2.36 (d, 1H, J=13.0 Hz); 2.61–2.89 (dt, 1H, J=3.2, 12.9 Hz); 3.42 (brt, 1H, J=12.8 Hz); 5.08 (ddd, 1H, J=5.2,7.2,12.3); 5.32 (d, 1H, J=5.4 Hz); 7.16–7.32 (m, 10H); Anal. (C30H39NO3) C, H, N.

Workup

extractionextracted with EtOAc (2×100 mL)
dry with materialThe organic phase was dried (MgSO4)
customevaporated to a clear oil which

Sources & evidence

ORD record: ord-a111b96ea0ef4e8d823152496eef5b07
Source dataset: uspto-grants-2006_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07056935B2

Reaction notes

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