(R)-(1-Methyl-pent-4-enyl)-carbamic acid benzyl ester synthesis
- Product Name:(R)-(1-Methyl-pent-4-enyl)-carbamic acid benzyl ester
- CAS Number:113774-91-7
- Molecular formula:C14H19NO2
- Molecular Weight:233.31
2622-05-1
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Yield:113774-91-7 73%
Reaction Conditions:
Stage #1: allylmagnesium bromidewith copper (I) bromide-dimethyl sulfide in tetrahydrofuran at -78; for 0.5 h;
Stage #2: ((R)-2-Iodo-1-methyl-ethyl)-carbamic Acid Benzyl Ester in tetrahydrofuran at -78 - -40; for 2.5 h;
Steps:
3.b
b. ((R)-1-Methyl-pent-4-enyl)-carbamic Acid Benzyl Ester Copper (I) bromide-dimethyl sulfide (1.93 g, 9.4 mmol) was dissolved in distilled THF (24 ml), then was cooled to -78 degrees C. A solution of alkyl magnesium chloride (9.4 ml, 2M in THF, Aldrich) was added dropwise, then the solution was stirred for 30 minutes. ((R)-2-Iodo-1-methyl-ethyl)arbamic acid benzyl ester (1.5 g, 4.7 mmol) in distilled THF (3 ml) was added dropwise, then the reaction was warmed to -40 degrees C. and was stirred for 2.5 h. The reaction mixture was quenched with aq. sat. NH4Cl (4 ml) at -40 degrees C., warmed to RT and the gray reaction mixture turned sky blue. THF was removed in vacuo. Then, Et2O was added and the reaction mixture was filtered to remove precipitated solids. The solids were washed with additional Et2O. The combined organics were extracted with 10% NH4OH (3*), then brine. The combined organics were dried with MgSO4, filtered, concentrated in vacuo, then filtered through a plug of silica gel washing with 20% EtOAc/hexanes (100 ml). The solution was concentrated in vacuo, then the resultant colorless oil was used in the next reaction without further purification (0.8 g, 73%).
References:
US2004/38965,2004,A1 Location in patent:Page/Page column 24
61425-27-2
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![Carbamic acid, N-[(1R)-1-methyl-2-[[(4-methylphenyl)sulfonyl]oxy]ethyl]-, phenylmethyl ester](/CAS/20210305/GIF/113707-74-7.gif)
113707-74-7
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113774-91-7
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