Carbamic acid, ethyl ester → (S)-5-[2-(tert-butyl-dimethyl-silanyloxy)-ethyl]-oxazolidin-2-one

HRID 527975Notes

Reaction equation

[C:1]([Si:5]([CH3:13])([CH3:12])[O:6][CH2:7][CH2:8][CH:9]1[CH2:11][O:10]1)([CH3:4])([CH3:3])[CH3:2].C([O:16][C:17](=O)[NH2:18])C.[N+](C1C=CC(C(O)=O)=CC=1)([O-])=O.[H-].[Na+]>>[C:1]([Si:5]([CH3:12])([CH3:13])[O:6][CH2:7][CH2:8][C@@H:9]1[O:10][C:17](=[O:16])[NH:18][CH2:11]1)([CH3:2])([CH3:3])[CH3:4]

Participants

Reactant 4

HCID 5641Carbamic acid, ethyl ester

HCID 61084-Nitrobenzoic Acid

HCID 24758Sodium hydride

HCID 11030897(R)-tert-butyldimethyl(2-(oxiran-2-yl)ethoxy)silane

Product 1

HCID 67349769(S)-5-[2-(tert-butyl-dimethyl-silanyloxy)-ethyl]-oxazolidin-2-oneYield 11%

Procedure

Starting from 2-[2-[[(tert-butyl)dimethylsilyl]oxy]ethyl]-oxirane, (7.00 g; prepared according to WO 2007/144423), carbamic acid ethyl ester (1.46 g), 4-nitrobenzoic acid (347 mg), (R,R)-(salen)CoII complex (626 mg) and NaH (1.676 g) and proceeding in analogy to Org. Letters (2005), 7, 1983-1985, the title compound was obtained as a dark orange solid (880 mg; 11% yield).

Sources & evidence

ORD record: ord-bdd3a8fb9d6d4db9aa1e43d36e268d5c
Source dataset: uspto-grants-2016_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09346804B2

Reaction notes

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