Propanal → (4S)-N-[(2S,3R)-2-vinyl-3-hydroxypentanoyl]-4-benzyl-2-oxazolidinone

HRID 1794564Notes

Reaction equation

[C:1]([N:6]1[C@@H:10]([CH2:11][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[CH2:9][O:8][C:7]1=[O:18])(=[O:5])/[CH:2]=[CH:3]/[CH3:4].C(N(CC)CC)C.[O-]S(C(F)(F)F)(=O)=O.C([B+]CCCC)CCC.[CH:43](=[O:46])[CH2:44][CH3:45]>C(Cl)Cl.CCCCCC.C(OCC)(=O)C>[CH:3]([C@@H:2]([C@H:43]([OH:46])[CH2:44][CH3:45])[C:1]([N:6]1[C@@H:10]([CH2:11][C:12]2[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=2)[CH2:9][O:8][C:7]1=[O:18])=[O:5])=[CH2:4]

Participants

Conditions

Temperature: 0 °C

Procedure

A solution of 2.45 g of (4S)-N-crotonyl-4-benzyl-2-oxazolidinone in 10 ml of anhydrous CH2Cl2 was cooled to −78° C., and 1.7 ml of triethylamine was added followed by 10.5 ml of a 1 M solution of dibutylboron triflate in CH2Cl2. After 30 minutes, the reaction was warmed to 0° C., kept for 20 minutes, then recooled to −78° C. Propionaldehyde (0.9 ml) was added, and the reaction was allowed to slowly warm to ambient temperature over 16 hours. Standard oxidative workup yielded the product (1.98 g, 65% yield) after chromatography (2:1 hexane/ethyl acetate). 1H-NMR (360 MHz, CDCl3): δ 7.2–7.35 (m,5H); 6.02 (1H,m); 5.41 (m,2H); 4.72 (m,1H); 4.58 (dd,1H); 4.20 (m,2H); 3.92 (m,1H); 3.25 (dd,1H); 2.98 (br s, 1H); 2.76 (dd,1H); 1.53 (m,2H); 0.98 (t,3H).

Workup

waitkept for 20 minutes
customrecooled to −78° C
temperatureto slowly warm to ambient temperature over 16 hours

Sources & evidence

ORD record: ord-de30b525f68b46089d213eedb7914f50
Source dataset: uspto-grants-2006_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07022825B2

Reaction notes

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