Diisopropylamine → HCID 18790064, compound

Temperature

-78 °C

Diisopropylamine (7.2 mL, 52 mmol) is dissolved in THF (85 mL), cooled to -78° C. and n-butyl lithium in hexanes (23 mL, 52 mmol) is added slowly. The reaction is allowed to warm to -30° C. over 15 minutes and is then recooled to -78° C. A solution of methyl isobutyrate (6 mL, 52 mmol) in THF (15 mL) is added dropwise over 20 minutes and then stirred an additional 40 minutes. Next solution of 5-phenylpentanal (7 g, 43 mmol) in THF (10 mL) is added dropwise over 10 minutes and the reaction is stirred 1 hour. Acetic acid (3 mL) is added slowly followed by a solution of NH4Cl (20 mL) and the reaction is allowed to warm to room temperature. The reaction is partitioned between ether (200 mL) and water (150 mL). The organic phase is washed with 1 N HCl (2×50 mL), NaHCO3 (50 mL) and brine (50 mL). The solution is dried over MgSO4 and concentrated in vacuo to provide methyl 3-hydroxy-2,2-dimethyl-7-phenylheptanoate (11.2, 99%): 1H NMR (300 MHz, CDCl3) δ 7.30-7.24 (m, 2H), 7.18-7.16 (m, 3H), 3.68 (s, 3H), 3.60 (dd, J=9.7, 1.9 Hz, 1H), 2.61 (t, J=7.5 Hz, 2H), 2.37 (s, 1H), 1.73-1.20 (m, 6H), 1.17 (s, 3H), 1.15 (s, 3H); MS (EI) m/e 264 (M+).

1. temperatureto warm to -30° C. over 15 minutes
2. customis then recooled to -78° C
3. stirringthe reaction is stirred 1 hour
4. temperatureto warm to room temperature
5. customThe reaction is partitioned between ether (200 mL) and water (150 mL)
6. washThe organic phase is washed with 1 N HCl (2×50 mL), NaHCO3 (50 mL) and brine (50 mL)
7. dry with materialThe solution is dried over MgSO4
8. concentrationconcentrated in vacuo

ORD record

ord-05a9e54365834cffb1537618eacd3086

Source dataset

uspto-grants-2000_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06057369