(S)-(-)-N-Benzyl-1-phenylethylamine → (S)-tert-Butyl 3-(benzyl((S)-1-phenylethyl)amino)heptanoate

HRID 2387788Notes

Reaction equation

HRID 2387788 reaction equation
C([Li])CCC.[CH2:6]([NH:13][C@H:14]([C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)[CH3:15])[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1.[C:22]([O:30][C:31]([CH3:34])([CH3:33])[CH3:32])(=[O:29])/[CH:23]=[CH:24]/[CH2:25][CH2:26][CH2:27][CH3:28]>C1COCC1>[CH2:6]([N:13]([C@H:14]([C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)[CH3:15])[C@@H:24]([CH2:25][CH2:26][CH2:27][CH3:28])[CH2:23][C:22]([O:30][C:31]([CH3:32])([CH3:33])[CH3:34])=[O:29])[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1

Participants

5

Reactant 3

HCID 1268085(S)-(-)-N-Benzyl-1-phenylethylamineHCID 15636290(E)-tert-Butyl hept-2-enoateHCID 178418339Butyllithium

Product 1

HCID 68104424(S)-tert-Butyl 3-(benzyl((S)-1-phenylethyl)amino)heptanoateYield 69.6%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

n-Butyllithium (2.5M in hexanes, 27.66 ml) was added to a stirred solution of (S)—N-benzyl-1-phenylethanamine (15.59 g) in THF (150 mL) at −78° C. The reaction mixture was stirred for 30 mins then the product from step (i) (8.5 g) in THF (50 mL) was added and the reaction mixture stirred for 2 h at −78° C. The mixture was quenched with sat. NH4Cl solution and warmed to rt. The product was partitioned between EtOAc and water, the organic phase was washed with water, dried, and evaporated. The residue was purified by column chromatography eluting with 5% EtOAc in isohexane to give the subtitle compound 12.7 g.

Workup

  1. stirringthe reaction mixture stirred for 2 h at −78° C
  2. customThe mixture was quenched with sat. NH4Cl solution
  3. customThe product was partitioned between EtOAc and water
  4. washthe organic phase was washed with water
  5. customdried
  6. customevaporated
  7. customThe residue was purified by column chromatography
  8. washeluting with 5% EtOAc in isohexane

Sources & evidence

ORD record
ord-99bbff74eb0043e787316cf18dfe97da
Source dataset
uspto-grants-2012_09
Patent number
US08268990B2

Reaction notes

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