HCID 57516721, compound → HCID 58464064, compound

HRID 1966570Notes

Reaction equation

HRID 1966570 reaction equation
[CH2:1]([N:8]([CH2:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)[CH2:9][C:10](=[O:15])[C:11]([CH3:14])([CH3:13])[CH3:12])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH3:23][Mg]Br>C(OCC)C>[CH2:1]([N:8]([CH2:16][C:17]1[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=1)[CH2:9][C:10]([CH3:23])([OH:15])[C:11]([CH3:14])([CH3:13])[CH3:12])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 57516721HCID 57516721, compoundHCID 178418573HCID 178418573, compound

Product 1

HCID 58464064HCID 58464064, compoundYield 71.3%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Conditions

Temperature
2.5 °C

Procedure

(1.6 g, 5.4 mmol) 1-Dibenzylamino-3,3-dimethyl-butan-2-one (Example 19, step 1) was dissolved in diethylether (20 ml) and cooled to 0-5° C. Methylmagnesium bromide (3M in diethylether) (2.2 ml, 6.5 mmol, 1.2 equiv.) was added drop wise at 0-5° C. and the mixture was stirred for 72 hours at room temperature. The reaction mixture was extracted with sat. NH4C1-solution and two times EtOAc. The organic layers were extracted with water, dryed over Na2SO4, filtered and evaporated to dryness. The crude material was purified by flash chromatography on silica gel (50 gr, ethyl acetate/heptane gradient, 0:100 to 100:0). The desired (RS)-1-dibenzylamino-2,3,3-trimethyl-butan-2-ol (1.2 g, 71% yield) was obtained as a yellow oil, MS: m/e=312.4 (M+H+).

Workup

  1. extractionThe reaction mixture was extracted with sat. NH4C1-solution and two times EtOAc
  2. extractionThe organic layers were extracted with water
  3. filtrationfiltered
  4. customevaporated to dryness
  5. customThe crude material was purified by flash chromatography on silica gel (50 gr, ethyl acetate/heptane gradient, 0:100 to 100:0)

Sources & evidence

ORD record
ord-963e65bef0d048a495a8a66ed2dd5078
Source dataset
uspto-grants-2013_04
Patent number
US08420661B2

Reaction notes

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