Methyl iodide → (2S,3R)-1-(tert-butyldimethylsilyl)-3-methyl-4-oxoazetidine-2-carboxylic acid

HRID 1783422Notes

Reaction equation

[Si:1]([N:8]1[C:11](=[O:12])[CH2:10][C@H:9]1[C:13]([OH:15])=[O:14])([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].[Li+].[CH3:17]C([N-]C(C)C)C.CI>C1COCC1>[Si:1]([N:8]1[C:11](=[O:12])[C@H:10]([CH3:17])[C@H:9]1[C:13]([OH:15])=[O:14])([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2]

Participants

Conditions

Temperature: -78 °C

Procedure

To a solution of (S)-1-(tert-butyldimethylsilyl)-4-oxoazetidine-2-carboxylic acid 4 (2.00 g, 8.73 mmol.) in THF (30 ml) at −78° C. was added LDA (19 ml, 2.0 eq.). After the solution was stirred for 20 min. at −78° C., it was warmed to 0° C. for 5 min. The solution was re-cooled to −78° C. and methyl iodide (3.10 g, 2.5 eq.) in THF (5 ml) was added. The reaction solution was warmed up to room temperature, quenched with aqueous KHSO4 solution (10%, 30 ml), extracted with ethyl acetate (3×). The combined organic layers were washed with brine twice and dried with MgSO4. After concentrating in vacuo, 47 was obtained. H1NMR (CDCl3): 0.15, 0.35 (s, 6H), 1.14 (s, 9H), 1.35 (d, 3H), 3.71 (d, 1H), 4.14 (m, 1H). C11H21NO3Si, Mol. Wt.: 243.37. Found: 244 (M+1).

Workup

temperatureit was warmed to 0° C. for 5 min
temperatureThe solution was re-cooled to −78° C.
temperatureThe reaction solution was warmed up to room temperature
customquenched with aqueous KHSO4 solution (10%, 30 ml)
extractionextracted with ethyl acetate (3×)
washThe combined organic layers were washed with brine twice
dry with materialdried with MgSO4
concentrationAfter concentrating in vacuo
custom47 was obtained

Sources & evidence

ORD record: ord-8b77a079ee394e79b7077d74f01c6326
Source dataset: uspto-grants-2009_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07501404B2

Reaction notes

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