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

HRID 1828069Notes

Reaction equation

C[O:2][C:3](=O)[C:4](=[O:29])[N:5]1[CH2:9][CH2:8][CH2:7][CH:6]1[C:10](=[O:28])[CH:11]([CH2:20][CH2:21][C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)[CH2:12][CH2:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1.[CH3:31][C:32]([Mg]Cl)([CH3:35])[CH2:33][CH3:34].[Cl-].[NH4+]>C1COCC1>[CH3:31][C:32]([CH3:35])([CH2:33][CH3:34])[C:3](=[O:2])[C:4]([N:5]1[CH2:9][CH2:8][CH2:7][CH:6]1[C:10](=[O:28])[CH:11]([CH2:20][CH2:21][C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)[CH2:12][CH2:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)=[O:29]

Participants

Conditions

Temperature: -78 °C

Procedure

To a solution of 0.18 g (0.45 mmol) of 12a in anhydrous THF (2 mL) was added dropwise at −78° C. a 1.0M solution of 2.2 mL (2.20 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 (3×100 mL). The organic phase was dried (MgSO4) and evaporated to a clear oil which was subject to column chromatography (EtOAc/Hexanes, 1:3) to yield 0.14 g (76.5%) of 13a as a clear oil. TLC Rf=0.5 (EtOAc/Hexanes, 1:3) 1H NMR (CDCl3, 400 MHz): δ 0.82–0.90 (m, 3H); 1.12–1.33 (m, 6H); 1.59–1.79 (m, 7H); 2.00–2.20 (m, 3H); 2.40–2.70 (t, 5H); 3.41–3.52 (m, 2H); 4.63–4.64 (m, 1H); 7.12–7.29 (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-bae8c92c64944f00a3176706743532c9
Source dataset: uspto-grants-2006_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07056935B2

Reaction notes

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