Tetrahydrofuran → HCID 67297220, compound

HRID 2384584Notes

Reaction equation

HRID 2384584 reaction equation
[CH2:1]([Mg]Br)[CH3:2].[CH3:5][N:6]([CH3:26])[CH2:7][C@H:8]([CH3:25])[C:9]([C:11]1[CH:16]=[CH:15][CH:14]=[C:13]([O:17][CH2:18][C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[CH:12]=1)=[O:10].C1C[O:30]CC1>>[CH3:26][N:6]([CH3:5])[CH2:7][C@H:8]([CH3:25])[C@:9]([C:11]1[CH:16]=[CH:15][CH:14]=[C:13]([O:17][C:18](=[O:30])[C:19]2[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=2)[CH:12]=1)([OH:10])[CH2:1][CH3:2]

Participants

4

Reactant 3

HCID 8028TetrahydrofuranHCID 25068202HCID 25068202, compound2×HCID 178418443HCID 178418443, compound

Product 1

HCID 67297220HCID 67297220, compoundYield 89%

Procedure

A solution of ethylmagnesiumbromide (1M in THF; 0.15 mol; 150 ml) was charged into a 500 ml 3 necked round-bottom flask with an over-head stirrer, a thermometer, inert gas supply and an addition funnel at 10° C. under nitrogen. To this solution (2S)-3-(dimethylamino)-1-(3-(benzyloxy)phenyl)-2-methyl-1-propanone (3) (33.0 g; 0.11 mol) dissolved in THF (150 ml) was added dropwise at 10-15° C. After the addition was finished the batch was stirred at room temperature for 16 h and quenched with ammonium hydrogensulfate solution (150 ml). The phases were separated and the aqueous phase was re-extracted with 3-pentanone (150 ml). The combined organic phases were dried over sodium sulfate and the solvent was removed completely on the rotary evaporator at 45-50° C. and <10 mbar. A yellowish oil was obtained in 89% yield (32.0 g). [α]=−10.5° C.

Workup

  1. customat 10° C.
  2. additionwas added dropwise at 10-15° C
  3. additionAfter the addition
  4. customquenched with ammonium hydrogensulfate solution (150 ml)
  5. customThe phases were separated
  6. extractionthe aqueous phase was re-extracted with 3-pentanone (150 ml)
  7. dry with materialThe combined organic phases were dried over sodium sulfate
  8. customthe solvent was removed completely on the rotary evaporator at 45-50° C.
  9. customA yellowish oil was obtained in 89% yield (32.0 g)
  10. custom[α]=−10.5° C.

Sources & evidence

ORD record
ord-16bf600978e347f79a65912ce6e4eac2
Source dataset
uspto-grants-2012_09
Patent number
US08263809B2

Reaction notes

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