Ammonium Chloride → HCID 57457828, compound

HRID 715116Notes

Reaction equation

HRID 715116 reaction equation
[CH2:1]([N:8]([CH2:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)[CH2:9][CH2:10][C:11]([O:13]CC)=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH2:23]([Mg]Br)[CH3:24].[NH4+].[Cl-]>C(OCC)C.CC(C)[O-].[Ti+4].CC(C)[O-].CC(C)[O-].CC(C)[O-]>[CH2:16]([N:8]([CH2:1][C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1)[CH2:9][CH2:10][C:11]1([OH:13])[CH2:24][CH2:23]1)[C:17]1[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=1

Participants

6

Reactant 3

HCID 25517Ammonium ChlorideHCID 44791227Ethyl 3-(dibenzylamino)propanoateHCID 178418443HCID 178418443, compound

Product 1

HCID 57457828HCID 57457828, compoundYield 88%

Reagents, catalysts & solvents 2

HCID 11026Titanium isopropoxideCatalystHCID 3283Diethyl EtherSolvent

Conditions

Temperature
0 °C

Procedure

Add titanium isopropoxide (860 mg, 3.03 mmol) to a solution of ethyl 3-(dibenzylamino)propanoate (9.0 g, 30.3 mmol) in ethyl ether, cool to 0° C., add ethyl magnesium bromide (3M in Et2O, 30.3 mL) drop-wise over 1 h, maintaining the temperature at ˜0-4° C., allow to warm to RT and stir overnight. Cool to 0° C., add satd. NH4Cl, stir at RT for 15 minutes, make basic with satd. NaHCO3 and extract with EtOAc (2×). Wash the combined organics with brine, dry over MgSO4, concentrate and purify via silica gel chromatography to give the title compound (7.5 g, 88%) as a pale yellow oil. 1H NMR (400 MHz, CDCl3): δ 7.20-7.15 (m, 8H), 7.12-7.07 (m, 2H), 3.45 (s, 4H), 2.61-2.59 (m, 2H), 1.57 (t, J=5.6 Hz, 2H), 0.36-0.33 (m, 2H), 0.30-0.17 (m, 2H).

Workup

  1. temperaturemaintaining the temperature at ˜0-4° C.
  2. temperatureto warm to RT
  3. temperatureCool to 0° C.
  4. additionadd
  5. extractionNaHCO3 and extract with EtOAc (2×)
  6. washWash the combined organics with brine
  7. dry with materialdry over MgSO4
  8. concentrationconcentrate
  9. custompurify via silica gel chromatography

Sources & evidence

ORD record
ord-f5670f12aabd456d813500d0802087ae
Source dataset
uspto-grants-2015_11
Patent number
US09187474B2

Reaction notes

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