2-Amino-2-methyl-1-propanol → (2R,3R)-2-(3-chlorophenyl)-3,5,5-trimethyl-2-morpholinol

HRID 11208

Reaction equation

HRID 11208 reaction equation
Br[CH:2]([CH3:12])[C:3]([C:5]1[CH:10]=[CH:9][CH:8]=[C:7]([Cl:11])[CH:6]=1)=[O:4].[NH2:13][C:14]([CH3:18])([CH3:17])[CH2:15][OH:16]>CO>[Cl:11][C:7]1[CH:6]=[C:5]([C@@:3]2([OH:4])[O:16][CH2:15][C:14]([CH3:18])([CH3:17])[NH:13][C@@H:2]2[CH3:12])[CH:10]=[CH:9][CH:8]=1

Participants

4

Reactant 2

HCID 118072-Amino-2-methyl-1-propanolHCID 4992116alpha-Bromo-3-chloropropiophenone

Product 1

HCID 9943908(2R,3R)-2-(3-chlorophenyl)-3,5,5-trimethyl-2-morpholinolYield 75%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

To a solution of 2-bromo-3′-chloropropiophenone (19.3 g, 0.08 mol) in MeOH (100 mL) was added dropwise a solution of 2-amino-2-methyl-1-propanol (27.8 g, 0.31 mol) in methanol (200 mL) at ambient temperature. The mixture was stirred for 18 h and concentrated in vacuo. The residue was partitioned between water and diethyl ether. The combined organic phase was extracted with 10% aqueous hydrogen chloride. The combined aqueous acid extracts were chilled in an ice bath and made basic with 40% aqueous sodium hydroxide. The mixture was extracted with diethyl ether, the combined diethyl ether extracts were washed with water and saturated sodium chloride solution, dried (K2CO3) and concentrated in vacuo to give 15.0 g (75%) of (+/−)-(2R*,3R*)-2-(3-chlorophenyl)-3,5,5-trimethyl-2-morpholinol as an off-white solid.

Workup

  1. concentrationconcentrated in vacuo
  2. customThe residue was partitioned between water and diethyl ether
  3. extractionThe combined organic phase was extracted with 10% aqueous hydrogen chloride
  4. temperatureThe combined aqueous acid extracts were chilled in an ice bath
  5. extractionThe mixture was extracted with diethyl ether
  6. washthe combined diethyl ether extracts were washed with water and saturated sodium chloride solution
  7. dry with materialdried (K2CO3)
  8. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-d55caad6b3ba44ea8fbfd252d937eada
Source dataset
uspto-grants-2006_08
Patent number
US07098206B2

Linked notes

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