Iodoethane → HCID 86620814, compound

HRID 250792Notes

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)C.ClC(Cl)(Cl)[C@H]1OC(=O)[C@H]2N1CCC2.ICC>>[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])[CH3:15]

Participants

Reactant 4

HCID 6340Iodoethane

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 86620814HCID 86620814, compoundYield 46%

Procedure

The reaction was carried out following a similar procedure to that described for the preparation of oxazolidinone 8 using n-butyllithium (1.31 M, 28.3 cm3, 37.1 mmol), diisopropylamine (5.2 cm3, 37.1 mmol), oxazolidinone 7 (6.0 g, 24.7 mmol) and iodoethane (5.9 cm3, 73.8 mmol) to afford oxazolidinone 9 (3.05 g, 46%) as a light red oil that solidified on standing to a pale brown solid: mp 76-77° C.: [α]D +18.5 (c 0.25 in CHCl3): δH (300 MHz; CDCl3) 1.04 (3 H, t, J 7.5, CH3), 1.60-1.80 (1H, m, CHAHBCH3), 1.72-1.99 (4H, m, CHAHBCH3, Proβ-HAHB and Proγ-H2), 2.20-2.30 (1H, m, Proβ-HAHB), 3.22-3.29 (2H, m, Proδ-H2) and 5.00 (1 H, s, NCH); δC (75 MHz; CDCl3) 8.4 (CH3, CH3), 25.5 (CH2, CH2CH3), 30.9 (CH2, Proγ-C), 35.6 (CH2, Proβ-C), 58.6 (CH2, Proδ-C), 72.5 (quat., Proα-C), 100.9 [quat., C(Cl3)], 102.5 (CH, NCH) and 176.9 (quat., CO); m/z (EI+) 272.0014 (MH+.C9H1335ClN3O2 requires 272.0012).

Sources & evidence

ORD record: ord-f6012d50ecbe456182759da025cfc0d3
Source dataset: uspto-grants-2011_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07863304B2

Reaction notes

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