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

HRID 1828063Notes

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.[C:32]([Mg]Cl)([CH3:35])([CH3:34])[CH3:33].[Cl-].[NH4+]>C1COCC1>[CH3:33][C:32]([CH3:35])([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 0.16 g (0.38 mmol) of 5 in anhydrous THF (2 mL) was added dropwise at −78° C. a 2.0M solution of 0.21 mL (0.42 mmol) of tert-butyl 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 (3×100 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 0.13 g (76.5%) of 6 as a clear oil. TLC Rf=0.62 (EtOAc/Hexanes, 1:4) 1H NMR (CDCl3, 300 MHz): δ 1.40 (s, 9H); 1.36–2.29 (m, 9H); 2.62–2.82 (m, 4H); 3.39–3.52 (m, 2H); 5.18 (m, 1H); 5.31 (d, 1H, J=6.2); 5.42 (d, 1H, J=5.2); 7.42–7.26 (m, 10H); Anal. (C29H37NO3) C, H, N.

Workup

extractionextracted with EtOAc (3×100 mL)
dry with materialThe organic phase was dried (MgSO4)
customevaporated to a clear oil which

Sources & evidence

ORD record: ord-3e5bbad024034906871c01f4ae143d78
Source dataset: uspto-grants-2006_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07056935B2

Reaction notes

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