Bromide ion → HCID 66856884, compound

HRID 2037496Notes

Reaction equation

HRID 2037496 reaction equation
COC(=O)[N:4]([CH:12]([C:14]1[CH:19]=[CH:18][C:17]([Br:20])=[CH:16][CH:15]=1)[CH3:13])[CH2:5][CH2:6][C:7](=[O:11])[CH:8]([CH3:10])[CH3:9].[Br-].[CH2:23]1[CH2:27]OC[CH2:24]1>>[Br:20][C:17]1[CH:16]=[CH:15][C:14]([CH:12]([NH:4][CH2:5][CH2:6][C:7]([OH:11])([CH2:27][CH:23]=[CH2:24])[CH:8]([CH3:9])[CH3:10])[CH3:13])=[CH:19][CH:18]=1

Participants

4

Reactant 3

HCID 259Bromide ionHCID 8028TetrahydrofuranHCID 66857182HCID 66857182, compound

Product 1

HCID 66856884HCID 66856884, compound

Procedure

To a solution of [1-(4-bromo-phenyl)-ethyl]-(4-methyl-3-oxo-pentyl)-carbamic acid methyl ester (1.78 g, 5 mmol) in dried THF (20 mL) was added allymagnesium bromide (1 M, 25 mL, 25 mmol) dropwise at −78° C. The mixture was stirred overnight. The reaction was quenched with aqueous sat. NH4Cl. The mixture was extracted with EtOAc. The organic phase was dried over Na2SO4, and condensed to give 3-{2-[1-(4-bromo-phenyl)-ethylamino]-ethyl}-2-methyl-hex-5-en-3-ol (2.2 g, crude).

Workup

  1. customThe reaction was quenched with aqueous sat. NH4Cl
  2. extractionThe mixture was extracted with EtOAc
  3. dry with materialThe organic phase was dried over Na2SO4, and condensed

Sources & evidence

ORD record
ord-332d5f8d2f534f0cb947a939581d8c4e
Source dataset
uspto-grants-2013_11
Patent number
US08575156B2

Reaction notes

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