Methyl iodide → HCID 118931314, compound

To a solution of (S)-2-(Isoindolin-2-yl) but-3-en-1-ol (FIG. 2, No. 3)(2.0 g, 9.2 mmol) in 40 mL DMF was successively added NaH (442 mg, 18.4 mmol) at 0° C., stirred for ten minutes followed by addition of MeI (1.73 mL, 27.6 mmol) and then the reaction mixture was stirred at room temperature for 3 h. The reaction mixture was quenched by addition of ice cold water, extracted with diethyl ether, washed with brine and dried over anhydrous MgSO4. The organic layer was then concentrated in vacuo and purified by silica gel column chromatography using ethyl acetate/hexane (1:9) as eluent to furnish 1.83 g (86%) yield of (S)-2-(1-Methoxybut-3-en-2-yl) isoindoline (FIG. 2, No. 4) as a crystalline white solid. [Rf=0.56, ethyl acetate/hexane (3:7)]; [α]D25 −75.1 (c 1.0, CH2Cl2); IR (CH2Cl2) v: 1773, 1708, 1468, and 1384 cm−1; 1H NMR (400 MHz, CDCl3) δ:3.3 (s, 3H), 3.6 (m, 1H), 4.06 (m, 1H), 5.0 (m, 1H), 5.22-5.31 (m, 2H), 6.12 (ddd, J=7.32 Hz, 1H), 7.68 (dd, J=2.76, 5.48 Hz, 2H), 7.80 (dd, J=2.76, 5.48 Hz, 2H); 13C NMR (100 MHz, CDCl3) δ: 52.8, 58.7, 71.3, 119.0, 123.2, 131.9, 132.1, 133.9, 168.0; HRMS (ESI-TOF) m/z calcd for C13H13NO3Na [M+Na+] 254.080. Found 254.079.

1. customat 0° C.
2. stirringthe reaction mixture was stirred at room temperature for 3 h
3. customThe reaction mixture was quenched by addition of ice cold water
4. extractionextracted with diethyl ether
5. washwashed with brine
6. dry with materialdried over anhydrous MgSO4
7. concentrationThe organic layer was then concentrated in vacuo
8. custompurified by silica gel column chromatography

ORD record

ord-6af1401f17c0460aa7558a218f2c456c

Source dataset

uspto-grants-2016_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09284263B1