Allyl bromide → (2S,3R)-3-allyl-1-(tert-butyldimethylsilyl)-3-methyl-4-oxoazetidine-2-carboxylic acid

HRID 1783423Notes

Reaction equation

[Si:1]([N:8]1[C:11](=[O:12])[C@H:10]([CH3:13])[C@H:9]1[C:14]([OH:16])=[O:15])([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].[Li+].[CH3:18][CH:19]([N-]C(C)C)C.[CH2:25](Br)C=C>C1COCC1>[CH2:13]([C@@:10]1([CH3:25])[C:11](=[O:12])[N:8]([Si:1]([C:4]([CH3:6])([CH3:5])[CH3:7])([CH3:3])[CH3:2])[C@@H:9]1[C:14]([OH:16])=[O:15])[CH:18]=[CH2:19]

Participants

Conditions

Temperature: -20 °C

Procedure

To a solution of compound 47 (0.200 g, 0.823 mmol) in THF (5 ml) at −78° C. was added a solution of LDA (1.10 ml, 2.4 eq.). The reaction solution was stirred for 20 min. at that temperature, warmed to −20° C. and allyl bromide (0.138 Ml, 2.0 eq.) was added slowly. Reaction mixture was warmed to 0° C. for 30 min. and quenched with KHSO4 (20 ml, 10%), extracted with ethyl acetate (3×). Combined organic layers were washed with brine twice and dried over MgSO4. After concentrating in vacuo, compound 48 was obtained. H1NMR (CDCl3): 0.15, 0.37 (s, 6H), 1.16 (s, 9H), 1.33 (s, 3H), 2.50 (m, 2H), 3.98 (s, 1H), 5.22 (m, 2H), 5.88 (m, 1H). C14H25NO3Si, Mol. Wt.: 283.44. Found: 284 (M+1).

Workup

customReaction mixture
temperaturewas warmed to 0° C. for 30 min.
customquenched with KHSO4 (20 ml, 10%)
extractionextracted with ethyl acetate (3×)
washCombined organic layers were washed with brine twice
dry with materialdried over MgSO4
concentrationAfter concentrating in vacuo

Sources & evidence

ORD record: ord-7f36e59fb3184c3a9cf914e071e4f31f
Source dataset: uspto-grants-2009_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07501404B2

Reaction notes

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