1,2-Dichloroethane → HCID 67486005, compound

HRID 1430625Notes

Reaction equation

HRID 1430625 reaction equation
[CH2:1]([O:3][C:4](=[O:16])[C:5]([O:8][C:9]1[CH:14]=[CH:13][CH:12]=[C:11]([NH2:15])[CH:10]=1)([CH3:7])[CH3:6])[CH3:2].Cl[CH2:18][CH2:19]Cl.[C:21](O)(=O)C.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>>[CH2:1]([O:3][C:4](=[O:16])[C:5]([O:8][C:9]1[CH:14]=[CH:13][CH:12]=[C:11]([NH:15][CH:18]([CH3:19])[CH3:21])[CH:10]=1)([CH3:7])[CH3:6])[CH3:2]

Participants

5

Reactant 4

HCID 111,2-DichloroethaneHCID 176Acetic AcidHCID 5049666Sodium triacetoxyborohydrideHCID 22060556HCID 22060556, compound

Product 1

HCID 67486005HCID 67486005, compoundYield 60%

Conditions

Temperature
0 °C

Procedure

To a solution of 2-(3-Amino-phenoxy)-2-methyl-propionic acid ethyl ester (0.2 g, 0.89 mmol) in 1,2-dichloroethane (3 ml) acetone (6.6 ml, 89.6 mmol) and acetic acid (0.053 g, 0.89 mmol) were added. The reaction mixture was cooled to 0° C. Sodium triacetoxyborohydride (0.266 g, 1.25 mmol) was added and stirred at r.t. for 24 h. The reaction mixture was quenched with saturated NaHCO3 and extracted in DCM (20 ml), washed with brine, dried over Na2SO4 and concentrated under reduced pressure to obtain crude product. Purification on silica gel (MeOH:CHCl3) yielded 0.14 g (60%) of 2-(3-Isopropylamino-phenoxy)-2-methyl-propionic acid ethyl ester which was hydrolyzed using a typical procedure A1 and used as such for the next step.

Workup

  1. customThe reaction mixture was quenched with saturated NaHCO3
  2. extractionextracted in DCM (20 ml)
  3. washwashed with brine
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated under reduced pressure
  6. customto obtain crude product
  7. customPurification on silica gel (MeOH:CHCl3)

Sources & evidence

ORD record
ord-9f5cc03f157140738ee30826306edec3
Source dataset
uspto-grants-2015_01
Patent number
US08940900B2

Reaction notes

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