Water → HCID 86693767, compound

HRID 245051Notes

Reaction equation

HRID 245051 reaction equation
[CH2:1]([N:8]([CH2:15][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)[C@H:9]1[CH2:13][CH2:12][CH2:11][C:10]1=[O:14])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH3:22][Mg]Br.O>C(OCC)C.Cl>[CH2:15]([N:8]([CH2:1][C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1)[C@H:9]1[CH2:13][CH2:12][CH2:11][C@@:10]1([CH3:22])[OH:14])[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1

Participants

6

Reactant 3

HCID 962WaterHCID 86693765HCID 86693765, compoundHCID 178418573HCID 178418573, compound

Product 1

HCID 86693767HCID 86693767, compoundYield 40%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolvent2×HCID 3283Diethyl EtherSolvent

Conditions

Temperature
-78 °C

Procedure

To a solution of (2S)-2-(dibenzylamino)cyclopentanone (8.31 g, 29.7 mmol) in diethyl ether (149 mL) at −78° C. is added methyl magnesium bromide (29.7 mL, 89.1 mmol, 3 M in diethyl ether) slowly. The mixture is stirred at −78° C. for 4 h and then the reaction is allowed to warm to room temperature. Water is added to the reaction, resulting in an emulsion. Aqueous 1 M hydrochloric acid is added to break up the emulsion while keeping the aqueous phase basic. The aqueous phase is extracted twice with EtOAc. The combined organic portions are dried over sodium sulfate, filtered, and concentrated under reduced pressure. The resulting residue is purified by silica gel chromatography (10% EtOAc/hexanes) to obtain the product. The material is dissolved in 1 M hydrochloric acid and extracted four times with EtOAc. The combined organic layers are dried over sodium sulfate, filtered, and concentrated under reduced pressure to afford the title compound as an orange solid (3.49 g, 40%). ES/MS m/z 296 (M+1).

Workup

  1. temperatureto warm to room temperature
  2. customresulting in an emulsion
  3. extractionThe aqueous phase is extracted twice with EtOAc
  4. dry with materialThe combined organic portions are dried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. customThe resulting residue is purified by silica gel chromatography (10% EtOAc/hexanes)
  8. customto obtain the product
  9. extractionextracted four times with EtOAc
  10. dry with materialThe combined organic layers are dried over sodium sulfate
  11. filtrationfiltered
  12. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-485c0cf70ad24723b01e109a1273ebed
Source dataset
uspto-grants-2014_02
Patent number
US08658693B2

Reaction notes

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