Dimethyl Sulfoxide → HCID 53818101, compound

HRID 1773086Notes

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(C)(C)C)=[O:12].C(N(CC)CC)C>ClCCl>[CH:20]([C@@H:19]1[CH2:22][CH2:23][CH2:24][N:18]1[C:11]([OH:13])=[O:12])=[O:21]

Participants

Conditions

Temperature: -78 °C

Procedure

A 2 L, 3-necked round bottomed flask equipped with an overhead stirrer and a N2 inlet was charged with a solution of oxalyl chloride (130 mL, 0.26 mol) in dichloromethane (250 mL). The solution was cooled to −78° C., and a solution of DMSO (20 mL, 0.28 mol) in dichloromethane (30 mL) was added dropwise. After 30 minutes, a solution of (S)—N-Boc-prolinol, Int-7a (40 g, 0.20 mol) in dichloromethane (200 mL) was added dropwise. After 30 minutes, triethylamine (140 mL, 1.00 mol) was added to the solution, and the flask was transferred to an ice/water bath and allowed to stir for another 30 minutes. The reaction mixture was diluted with dichloromethane (200 mL) and washed successively with H2O, 1M HCl, saturated NaHCO3, and brine. The organic layer was dried over Na2SO4, filtered, and concentrated in vacuo to provide crude (S)-2-formyl-pyrrolidine-1-carboxylic acid tort-butyl ester, Int-7b (40 g) as oil, which was used without further purification.

Workup

customA 2 L, 3-necked round bottomed flask equipped with an overhead stirrer and a N2 inlet
waitAfter 30 minutes
customthe flask was transferred to an ice/water bath
washwashed successively with H2O, 1M HCl, saturated NaHCO3, and brine
dry with materialThe organic layer was dried over Na2SO4
filtrationfiltered
concentrationconcentrated in vacuo

Sources & evidence

ORD record: ord-b3a92bc9e2614c71b13f55dc7ad15356
Source dataset: uspto-grants-2016_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09254292B2

Reaction notes

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