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

HRID 1617137Notes

Reaction equation

HRID 1617137 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 ml1) 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-3b3242bb291c4f2db5c0e038618d98c9
Source dataset
uspto-grants-2014_07
Patent number
US08765939B2

Reaction notes

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