Methanol → HCID 45097414, compound

Lithium borohydride (6.6 mmol, 3.31 mL of a 2M in THF solution) was added dropwise to an ice cold THF solution of 1-(1,1-dimethylethyl) 2-ethyl(2S,3S)-3-methyl-1,2-pyrrolidinedicarboxylate (850 mg, 3.3 mmol) and methanol (0.133 mL, 3.3 mmol). The reaction was warmed to room temperature and then stirred for 4 hours. The reaction was quenched with i-propanol then with saturated NaHCO3. The reaction mixture was extracted 3× with ethyl acetate. The organic layers were dried over MgSO4 and concentrated under reduced pressure to give the title compound, which was used without further purification. 1H NMR (400 MHz, DMSO-D6) δ ppm 0.9 (t, J=7.0 Hz, 3 H) 1.3 (m, 9 H) 1.9 (m, 1 H) 2.2 (m, 1 H) 3.1 (m, 2 H) 3.3 (m, 2 H) 3.5 (m, 1 H) 4.7 (m, 1 H).

1. customThe reaction was quenched with i-propanol
2. extractionThe reaction mixture was extracted 3× with ethyl acetate
3. dry with materialThe organic layers were dried over MgSO4
4. concentrationconcentrated under reduced pressure

ORD record

ord-9a20564cf9fa41d0a0edc597be1f1e37

Source dataset

uspto-grants-2008_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07368453B2