Ammonium Chloride → HCID 59497521, compound

HRID 1747371

Reaction equation

HRID 1747371 reaction equation
[CH2:1]([NH:8][C@@H:9]([CH3:16])[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[Li]CCCC.[C:22]([O:29][CH2:30][CH3:31])(=[O:28])/[CH:23]=[CH:24]/[CH2:25][CH2:26][CH3:27].[NH4+].[Cl-]>C1COCC1>[CH2:30]([O:29][C:22](=[O:28])[CH2:23][C@@H:24]([N:8]([CH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1)[C@H:9]([C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)[CH3:16])[CH2:25][CH2:26][CH3:27])[CH3:31]

Participants

6

Reactant 4

HCID 25517Ammonium ChlorideHCID 1268085(S)-(-)-N-Benzyl-1-phenylethylamineHCID 5364778Ethyl trans-2-hexenoateHCID 178418339Butyllithium

Product 1

HCID 59497521HCID 59497521, compoundYield 50.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of (S)-(−)-N-benzyl-alpha-methyl-benzylamine (50 mL, 239 mmol) in THF (150 mL) at 0 C was added BuLi (2.5 M in THF) (100 mL, 250 mmol) under nitrogen atmosphere. The solution was cooled to −78 C and ethyl trans-2-hexenoate (16.6 g, 117 mmol) was added. The solution was stirred for 1 hour and Sat. NH4Cl solution was added. The solution was warmed to room temperature and was extracted with EtOAc. The combined organic layer was dried with MgSO4 and was filtered. The filtrate was concentrated and the residue was purified by CombiFlash with 5% EtOAc in Hexane as the eluent to afford the desirable product (S)-3-[Benzyl-((S)-1-phenyl-ethyl)-amino]-hexanoic acid ethyl ester (20.8 g, 50%) as a colorless oil.

Workup

  1. additionwas added
  2. extractionwas extracted with EtOAc
  3. dry with materialThe combined organic layer was dried with MgSO4
  4. filtrationwas filtered
  5. concentrationThe filtrate was concentrated
  6. customthe residue was purified by CombiFlash with 5% EtOAc in Hexane as the eluent

Sources & evidence

ORD record
ord-9d0e450047d74117a4b27ba2f4a828ad
Source dataset
uspto-grants-2015_10
Patent number
US09150556B2

Linked notes

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