Hydrochloric Acid → (S)-3-(Benzyl((S)-1-phenylethyl)amino)heptan-1-ol

HRID 2387790Notes

Reaction equation

HRID 2387790 reaction equation
[CH2:1]([N:8]([C@H:18]([C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)[CH3:19])[C@@H:9]([CH2:14][CH2:15][CH2:16][CH3:17])[CH2:10][C:11](O)=[O:12])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.B.O1CCCC1.CO.Cl>C1COCC1>[CH2:1]([N:8]([C@H:18]([C:20]1[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=1)[CH3:19])[C@@H:9]([CH2:14][CH2:15][CH2:16][CH3:17])[CH2:10][CH2:11][OH:12])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 887MethanolHCID 2723981Borane;tetrahydrofuranHCID 68414644(S)-3-(Benzyl((S)-1-phenylethyl)amino)heptanoic acid

Product 1

HCID 68752972(S)-3-(Benzyl((S)-1-phenylethyl)amino)heptan-1-olYield 52.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

The product from step (iii) (12 g) was dissolved in THF (120 mL) and borane-tetrahydrofuran complex (1M in THF, 132.3 ml) added dropwise. The reaction mixture was stirred at rt overnight then MeOH was added followed by 2M HCl (20 mL). The mixture was evaporated and the residue taken up in MeOH and purified via SCX resin and the residue was further purified via column chromatography eluting with 10-20% EtOAc in isohexane to give the subtitle compound 6 g.

Workup

  1. customThe mixture was evaporated
  2. custompurified via SCX resin
  3. customthe residue was further purified via column chromatography
  4. washeluting with 10-20% EtOAc in isohexane

Sources & evidence

ORD record
ord-997b1e34ac4646178d2a8f005f1bbd5d
Source dataset
uspto-grants-2012_09
Patent number
US08268990B2

Reaction notes

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