Water → HCID 53757433, compound

HRID 2166540Notes

Reaction equation

HRID 2166540 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([C@:9]2([OH:17])[CH2:14][CH2:13][CH2:12][CH2:11][C@H:10]2[NH:15][CH3:16])[CH:6]=[CH:7][CH:8]=1.C(N(CC)CC)C.O.[Br:26][CH:27]([CH3:31])[C:28](Br)=[O:29]>ClCCl>[Br:26][CH:27]([CH3:31])[C:28]([N:15]([C@@H:10]1[CH2:11][CH2:12][CH2:13][CH2:14][C@:9]1([C:5]1[CH:6]=[CH:7][CH:8]=[C:3]([O:2][CH3:1])[CH:4]=1)[OH:17])[CH3:16])=[O:29]

Participants

6

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 79047Propanoyl bromide, 2-bromo-HCID 13062044HCID 13062044, compound

Product 1

HCID 53757433HCID 53757433, compoundYield 104.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Crude (1R*,2R*)-1-(3-methoxyphenyl)-2-methylaminocyclohexanol (4.7 g, from Example 6) was dissolved in dichloromethane (50 cm3) containing triethylamine (2.8 cm3, 2.02 g). The solution was cooled to 10° in a bath of cold water and treated dropwise with 2-bromopropionyl bromide (2.33 cm3, 4.32 g). The mixture was stirred for 1 hr. while cooling and was then concentrated under reduced pressure to an oily solid. This was partitioned between N hydrochloric acid (50 cm3) and ether (50 cm3), and the aqueous phase was extracted with further ether (3×20 cm3). The ether extracts were dried (Na2SO4) and evaporated, leaving crude (1R*,2R*)-2-(2-bromopropionyl-N-methylamino)-1-(3-methoxyphenyl)cyclohexanol as a yellow oil (7.7 g).

Workup

  1. temperaturewhile cooling
  2. concentrationwas then concentrated under reduced pressure to an oily solid
  3. customThis was partitioned between N hydrochloric acid (50 cm3) and ether (50 cm3)
  4. extractionthe aqueous phase was extracted with further ether (3×20 cm3)
  5. dry with materialThe ether extracts were dried (Na2SO4)
  6. customevaporated

Sources & evidence

ORD record
ord-d8a6032607a44c95a08177b66bec401a
Source dataset
uspto-grants-1983_06
Patent number
US04387097

Reaction notes

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