(R)-tert-butyl 2-(4-bromophenyl)propylcarbamate synthesis

6synthesis methods

Product Name:(R)-tert-butyl 2-(4-bromophenyl)propylcarbamate
CAS Number:211315-53-6
Molecular formula:C14H20BrNO2
Molecular Weight:314.22

863453-61-6 Synthesis

(r)-tert-butyl 5-methyl-1,2,3-oxathiazolidine-3-carboxylate 2,2-dioxide

863453-61-6
75 suppliers
$62.00/100mg

589-87-7 Synthesis

589-87-7
529 suppliers
$10.00/1g

(R)-tert-butyl 2-(4-bromophenyl)propylcarbamate

211315-53-6
29 suppliers
$12.00/100mg

Yield:211315-53-6 62%

Reaction Conditions:

Stage #1: 1,4-bromoiodobenzenewith TurboGrignard in diethyl ether at -12; for 2 h;Inert atmosphere;
Stage #2: with copper(l) iodide in diethyl ether at -12; for 0.5 h;Inert atmosphere;
Stage #3: tert-butyl (5R)-5-methyl-2,2-dioxo-1,2λ⁶,3-oxathiazolidine-3-carboxylateoptical yield given as %ee;regioselective reaction;Further stages;

Steps:

General protocol for the preparation of compounds (3a-e) by reaction of m-(trifluoromethyl)phenylmagnesium chloride with sulfamidates (2a-e)

General procedure: To a 2M solution of isopropylmagnesium chloride (20 ml 0.040 mol) in diethyl ether was added 3-iodo benzotrifluoride (11.05 g 5.85 ml 0.040 mol) at -12°C and the mixture was kept in the freezer (-20°C) for 18h. To the resulting clear solution was added 0.100 g cuprous (I) iodide (0.00032 mol) and the mixture was stirred at room temperature for 2h. A clear slighthly yellow solution was obtained.To a suspension of the corresponding sulfamidate (2a-e) (0.0050 mol) in 5 ml diethyl ether was added drop wise 5.0 ml of the stock solution of m-(trifluoromethyl)phenylmagnesium chloride (ca 0.001 mol) as prepared above at -12°C and the mixture was stirred at -12°C for 2h. To the resulting suspension was added 10 ml of a 10% aqueous citric acid solution and the mixture was stirred at room temperature for 0.5h. The phases were separated and the organic phase was dried over magnesium sulfate and evaporated to dryness. The resulting residue was purified by kugelrohr distillation (0.4 mBar; 95°C) or by recrystallisation from heptane as indicated in the table.

References:

Hebeisen, Paul;Weiss, Urs;Alker, André;Staempfli, Andreas [Tetrahedron Letters,2011,vol. 52,# 41,p. 5229 - 5233] Location in patent:supporting information; experimental part

24424-99-5 Synthesis

24424-99-5
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211315-53-6
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$12.00/100mg

(R)-2-(4-bromophenyl)propan-1-amine hydrochloride

211315-52-5
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References

99-90-1
464 suppliers
$6.00/25g

211315-53-6
29 suppliers
$12.00/100mg

References

6888-79-5
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211315-53-6
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References

Benzene, 1-bromo-4-[1-(bromomethyl)ethenyl]-

184773-89-5
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211315-53-6
29 suppliers
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References