HCID 86623842, compound → HCID 68711442, compound

HRID 1911533Notes

Reaction equation

HRID 1911533 reaction equation
[C:1]([O:5][C:6]([N:8]1[C@@H:12](/[CH:13]=[C:14](\Br)/[C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[CH2:11][O:10][C:9]1([CH3:23])[CH3:22])=[O:7])([CH3:4])([CH3:3])[CH3:2].[CH2:24]([Zn]CC)[CH3:25]>>[C:1]([O:5][C:6]([N:8]1[C@@H:12](/[CH:13]=[C:14](/[C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)\[CH2:24][CH3:25])[CH2:11][O:10][C:9]1([CH3:23])[CH3:22])=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

3

Reactant 2

HCID 86623842HCID 86623842, compoundHCID 178418750HCID 178418750, compound

Product 1

HCID 68711442HCID 68711442, compound

Procedure

In analogy to example 162c (S)-4-((Z)-2-bromo-2-phenyl-vinyl)-2,2-dimethyl-oxazolidine-3-carboxylic acid tert-butyl ester was reacted with diethylzinc to give (S)-2,2-dimethyl-4-((E)-2-phenyl-but-1-enyl)-oxazolidine-3-carboxylic acid tert-butyl ester. Colourless oil. MS (ISP): 332.3 ([M+H]+).

Sources & evidence

ORD record
ord-5bb77c0b3402458b9671ec7c5527df9d
Source dataset
uspto-grants-2013_12
Patent number
US08604061B2

Reaction notes

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