Aluminium lithium hydride → HCID 86679680, compound

To a stirred solution of (cis)-5-benzyl-3a-methoxytetrahydropyrrolo[3,4-c]pyrrole-1,3(2H,3aH)-dione (400 mg, 1.54 mmol) in diethyl ether (7 mL), under nitrogen, was added LAH (7.92 mL, 1.0 M in diethyl ether) to form a white suspension that was stirred at ambient temperature for 21 hrs. The reaction was then cooled to 0° C. and quenched by the addition of water (0.3 mL), 15% NaOH (0.3 mL) and water (0.9 mL), as described by Fieser, L. F.; Fieser, M. Reagents for Organic Synthesis Vol. 1, Wiley, New York 1967, pp 581-595. The mixture was filtered and washed with EtOAc (100 mL). The filtrate was concentrated with toluene to give the crude title compound as a clear oil that was carried forward to the next step without further purification assuming quantitative yield. m/z (APCI+) for C14H20N2O 233.20 (M+H)+.

1. customto form a white suspension that
2. temperatureThe reaction was then cooled to 0° C.
3. customquenched by the addition of water (0.3 mL), 15% NaOH (0.3 mL) and water (0.9 mL)
4. customReagents for Organic Synthesis Vol. 1, Wiley, New York 1967, pp 581-595
5. filtrationThe mixture was filtered
6. washwashed with EtOAc (100 mL)
7. concentrationThe filtrate was concentrated with toluene

ORD record

ord-ade600e808094251a8bfc2555702e2c0

Source dataset

uspto-grants-2015_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09040547B2