Allyl bromide → (3R,7aR)-7a-Allyl-3-(trichloromethyl)tetrahydropyrrolo[1,2-c]oxazol-1(3H)-one

HRID 250793Notes

Reaction equation

[CH3:1][C@@:2]12[CH2:9][CH2:8][CH2:7][N:6]1[C@@H:5]([C:10]([Cl:13])([Cl:12])[Cl:11])[O:4][C:3]2=[O:14].[CH:15](NC(C)C)(C)[CH3:16].ClC(Cl)(Cl)[C@H]1OC(=O)[C@H]2N1CCC2.C(Br)C=C>>[CH2:1]([C@@:2]12[CH2:9][CH2:8][CH2:7][N:6]1[C@@H:5]([C:10]([Cl:13])([Cl:12])[Cl:11])[O:4][C:3]2=[O:14])[CH:15]=[CH2:16]

Participants

Reactant 4

HCID 7841Allyl bromide

HCID 7912Diisopropylamine

HCID 10944680HCID 10944680, compound

HCID 59428108(3R,7aS)-Tetrahydro-7a-methyl-3-(trichloromethyl)-1H,3H-pyrrolo[1,2-c]oxazol-1-one

Product 1

HCID 10859049(3R,7aR)-7a-Allyl-3-(trichloromethyl)tetrahydropyrrolo[1,2-c]oxazol-1(3H)-oneYield 60%

Procedure

(Wang et al. Synlett 1999, 1, 33) The reaction was carried out following a similar procedure to that described for the preparation of oxazolidinone 8 using n-butyllithium (1.31 M, 9.93 cm3, 13.0 mmol), diisopropylamine (1.82 cm3, 13.0 mmol), oxazolidinone 7 (2.10 g, 8.7 mmol) and allyl bromide (2.25 cm3, 26.0 mmol) to afford oxazolidinone 10 (1.48 g, 60%) as a light orange oil for which the NMR data were in agreement with the literature.

Sources & evidence

ORD record: ord-bd39e52385f147df872f48738dba2e0f
Source dataset: uspto-grants-2011_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07863304B2

Reaction notes

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