Dimethyl Sulfoxide → HCID 178461670, compound

A three neck, 250 mL round bottom flask was equipped with a low temperature thermometer and two (2) equalizing dropping funnels. One of these was connected to a nitrogen line and charged with a solution of ((R)-1-((S)-1-phenylethyl)aziridin-2-yl)methanol EBE 06046 (7.0 g, 39.5 mmol) in CH2Cl2 (75 mL), the other was charged with a solution of DMSO (9.25 g, 118.5 mmol) in CH2Cl2 (11 mL). To a solution of oxalyl chloride (7.5 g, 59.3 mmol) in CH2Cl2 (90 mL) under N2 at −78° C., the DMSO solution was added dropwise during 20 min and stirred for 20 min. EBE 06046 (7.0 g, 39.5 mmol) in CH2Cl2 (75 mL) was added dropwise over 50 min. then the dropping funnel was charged with DIEA (42.6 mL, 237 mmol) in CH2Cl2 (10 mL) and the reaction mixture was stirred for 30 min at −45° C. The DIEA solution was added over 5 min with the reaction mixture at −78° C. and the reaction was allowed to warm to room temperature. The reaction mixture was washed with H2O (3×50 mL), dried over MgSO4, filtered, evaporated. The crude product obtained was purified by column chromatography on silica with a gradient of 0-20% [v/v] EtOAc in cyclohexane to give (R)-1-((S)-1-phenylethyl)aziridine-2-carbaldehyde EBE 06048 as a yellow oil (5.59 g, 81% yield).

1. stirringthe reaction mixture was stirred for 30 min at −45° C
2. washThe reaction mixture was washed with H2O (3×50 mL)
3. dry with materialdried over MgSO4
4. filtrationfiltered
5. customevaporated
6. customThe crude product obtained
7. customwas purified by column chromatography on silica with a gradient of 0-20% [v/v] EtOAc in cyclohexane

ORD record

ord-288887f8bff24119b6e0b71ae8fd081e

Source dataset

uspto-grants-2016_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09399628B2