Dimethyl Sulfoxide → N-(tert-Butoxycarbonyl)-D-prolinal

Temperature

-78 °C

A flask containing DMSO (7.73 mL, 108.6 mmol) and CH2Cl2 (150 mL) under nitrogen is stirred at −78° C. A 2M solution of oxalyl chloride in CH2Cl2 (36.25 mL, 72.5 mmol) is added dropwise and the reaction is stirred for 10 minutes at −78° C. A solution of Boc-D-prolinol (7.05 g, 35.02 mmol) in CH2Cl2 (70 mL) was added dropwise and the reaction stirred at −78° C. for 20 minutes. Triethylamine (19.53 mL, 140 mmol) was added to the mixture and the reaction allowed to warm to RT. The reaction was poured into H2O (40 mL) and the organic phase removed. The aqueous phase was saturated with NaCl and extracted with CH2Cl2 (2×75 mL). The organic fractions were combined, dried over MgSO4 and concentrated. Purification by flash chromatography 25% EtOAc/Hexanes gave the title compound as a yellow oil (6.70 g, 33.65 mmol). 1H NMR (CDCl3, 300 MHz) 9.45(d, 1H), 4.18, 4.04(two m, 1H), 3.62-3.35(m, 2H), 2.20-1.78(m, 4H), 1.46, 1.42(two s, 9H).

1. stirringthe reaction is stirred for 10 minutes at −78° C
2. stirringthe reaction stirred at −78° C. for 20 minutes
3. temperatureto warm to RT
4. customthe organic phase removed
5. extractionextracted with CH2Cl2 (2×75 mL)
6. dry with materialdried over MgSO4
7. concentrationconcentrated
8. customPurification by flash chromatography 25% EtOAc/Hexanes

ORD record

ord-cb51be841b4d4e4c8ba438362d461e03

Source dataset

uspto-grants-2008_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07361663B2