Dimethyl Sulfoxide → tert-butyl (2S)-2-formylpyrrolidine-1-carboxylate

HRID 1530735Notes

Reaction equation

C(Cl)(=O)C(Cl)=O.CS(C)=O.[C:11]([N:18]1[CH2:24][CH2:23][CH2:22][C@H:19]1[CH2:20][OH:21])([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:12]>C(Cl)Cl>[C:14]([O:13][C:11]([N:18]1[CH2:24][CH2:23][CH2:22][C@H:19]1[CH:20]=[O:21])=[O:12])([CH3:17])([CH3:16])[CH3:15]

Participants

Conditions

Temperature: -78 °C

Procedure

A 2 L, 3-necked round bottomed flask equipped with an overhead stir and a N2 inlet was charged with a solution of oxalyl chloride (130 mL, 0.26 mol) in DCM (250 mL). The solution was cooled to −78° C., and a solution of DMSO (20 mL, 0.28 mol) in DCM (30 mL) was added dropwise. After 30 minutes, a solution of (S)—N-Boc-prolinol (40 g, 0.20 mol) in DCM (200 mL) was added dropwise. After 30 minutes, TEA (140 mL, 1.00 mol) was added to the solution, and the flask was transferred to an ice/water bath and stirred for another 30 minutes. The reaction mixture was diluted with DCM (200 mL) and washed successively with H2O, 1M HCl, saturated NaHCO3, and brine. The DCM layer was dried over Na2SO4, filtered, and concentrated to afford crude (S)-2-formyl-pyrrolidine-1-carboxylic acid tert-butyl ester (40 g) as an oil, which was used without further purification.

Workup

customA 2 L, 3-necked round bottomed flask equipped with an overhead
waitAfter 30 minutes
customthe flask was transferred to an ice/water bath
stirringstirred for another 30 minutes
washwashed successively with H2O, 1M HCl, saturated NaHCO3, and brine
dry with materialThe DCM layer was dried over Na2SO4
filtrationfiltered
concentrationconcentrated

Sources & evidence

ORD record: ord-2cea2c2fe094470785c2a777a5e02a59
Source dataset: uspto-grants-2015_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09090661B2

Reaction notes

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