Diethyl Ether → HCID 86709170, compound

HRID 1851115Notes

Reaction equation

HRID 1851115 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](C)[C:10](OC)=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH3:22][Mg]I.CC[O:27][CH2:28][CH3:29]>>[CH2:15]([N:8]([CH2:1][C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1)[C@@H:9]([CH3:10])[C:28]([CH3:29])([OH:27])[CH3:22])[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1

Participants

4

Reactant 3

HCID 3283Diethyl EtherHCID 11414885HCID 11414885, compoundHCID 178418373HCID 178418373, compound

Product 1

HCID 86709170HCID 86709170, compound

Conditions

Temperature
0 °C

Procedure

(S)-Methyl 2-(dibenzylamino)propanoate (15.76 g, 55.6 mmol) was dissolved in Et2O (400 mL) and then cooled to ca. 0° C. Methylmagnesium iodide (27.7 mL, 3 M) was added next. The mixture turned heterogeneous white with addition of the latter. The mixture was allowed to warm to ambient temperature. LCMS the next day (17 h) indicated conversion to the desired product. The reaction was slowly quenched with sat. aqueous NH4Cl and then diluted with water and EtOAc. The layers were separated and the aqueous portion was further extracted with EtOAc. The combined organic portions were dried over Na2SO4, filtered and concentrated to a pale yellow oil. LCMS after thorough drying showed the desired product. This material was used directly for the next step: MS (ESI) m/z 284 (M+1).

Workup

  1. additionThe mixture turned heterogeneous white with addition of the latter
  2. temperatureto warm to ambient temperature
  3. customthe next day (17 h)

Sources & evidence

ORD record
ord-d8f0ad03c8bb41709bffc556fc064766
Source dataset
uspto-grants-2015_02
Patent number
US08957104B2

Reaction notes

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