Diisobutylaluminum hydride → HCID 89114986, compound

Temperature

-78 °C

A 25 mL round-bottomed flask was charged with methyl 6-(4-(((tert-butoxycarbonyl)amino)methyl)piperidin-1-yl)pyrimidine-4-carboxylate (150 mg, 0.43 mmol, 1 equiv.) and CH2Cl2 (2 mL). The reaction mixture was cooled to −78° C. DIBAL-H 1 M in CH2Cl2 (0.64 mL, 0.64 mmol, 1.5 equiv.) was added in 3 minutes at −78° C. The reaction was stirred for 4 h at −78° C. LC-MS showed some starting material. Another portion of DIBAL-H 1 M in CH2Cl2 (0.5 mL, 0.5 mmol, 1.2 equiv.) was added in 1 min at −78° C. LC-MS after 30 min showed the reaction was complete. The reaction was quenched at −78° C. after 40 min with methanol (1 mL). The solvents were concentrated in vacuo. The residue was partitioned between CH2Cl2 (10 mL) and 1 N NaOH (6 mL). The aqueous layer was extracted with CH2Cl2 (2×10 mL). The organic layer was dried over Na2SO4. The solvent was evaporated to give the crude desired aldehyde (77.9 mg, 56.8% crude yield) as an yellowish oil. The crude reaction aldehyde was carried on the next step without any further purification. LC-MS m/z 339 (M+1+H2O) and 351 (M+1+MeOH).

1. waitLC-MS after 30 min showed
2. customThe reaction was quenched at −78° C. after 40 min with methanol (1 mL)
3. concentrationThe solvents were concentrated in vacuo
4. customThe residue was partitioned between CH2Cl2 (10 mL) and 1 N NaOH (6 mL)
5. extractionThe aqueous layer was extracted with CH2Cl2 (2×10 mL)
6. dry with materialThe organic layer was dried over Na2SO4
7. customThe solvent was evaporated

ORD record

ord-426a9b0a72584de184fdb0710ef1acb1

Source dataset

uspto-grants-2014_12

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08901145B2