Methyl iodide → (2R,4R)-4-Methoxy-1-trityl-pyrrolidine-2-carboxylic acid methyl ester

HRID 2217457Notes

Reaction equation

[CH3:1][O:2][C:3]([C@H:5]1[CH2:9][C@@H:8]([OH:10])[CH2:7][N:6]1[C:11]([C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1)([C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)=[O:4].CI.[H-].[Na+].[CH3:34]COC(C)=O>CN(C=O)C.C1COCC1>[CH3:1][O:2][C:3]([C@H:5]1[CH2:9][C@@H:8]([O:10][CH3:34])[CH2:7][N:6]1[C:11]([C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1)([C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)[C:18]1[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=1)=[O:4]

Participants

Conditions

Temperature: 0 °C

Procedure

Into a solution of 2 (5.71 g, 14.7 mmol) in anhydrous DMF (20 mL) and anhydrous THF (20 mL) was added MeI (3.67 mL, 58.9 mmol). The solution was cooled to 0° C. in an ice bath and NaH (0.766 g, 19.2 mmol) was added in one portion. The mixture was stirred at RT for 26 h before adding EtOAc and washing sequentially with water and brine. The organic layer was dried over MgSO4 and concentrated under reduced pressure. Purification of the crude material by flash chromatography revealed 3 (4.67 g, 79%) as a white solid.

Workup

washwashing sequentially with water and brine
dry with materialThe organic layer was dried over MgSO4
concentrationconcentrated under reduced pressure
customPurification of the crude material by flash chromatography

Sources & evidence

ORD record: ord-fd7139d14ae64c2180b70720f1a27396
Source dataset: uspto-grants-2008_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07407972B2

Reaction notes

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