(1S,2S)-(1-([benzyloxycarbonyl-(2,4-dimethyl-benzyl)-amino]-methyl}-2-hydroxy-pentyl)-carbamic acid tert-butyl ester → (2S,3S)-2-amino-1-(2,4-dimethyl-benzylamino)-hexan-3-ol

HRID 1766845Notes

Reaction equation

HRID 1766845 reaction equation
C(OC(=O)[NH:7][C@@H:8]([CH2:14][N:15](C(OCC1C=CC=CC=1)=O)[CH2:16][C:17]1[CH:22]=[CH:21][C:20]([CH3:23])=[CH:19][C:18]=1[CH3:24])[C@@H:9]([OH:13])[CH2:10][CH2:11][CH3:12])(C)(C)C>CO.[Pd]>[NH2:7][C@H:8]([C@@H:9]([OH:13])[CH2:10][CH2:11][CH3:12])[CH2:14][NH:15][CH2:16][C:17]1[CH:22]=[CH:21][C:20]([CH3:23])=[CH:19][C:18]=1[CH3:24]

Participants

4

Reactant 1

HCID 69287833(1S,2S)-(1-([benzyloxycarbonyl-(2,4-dimethyl-benzyl)-amino]-methyl}-2-hydroxy-pentyl)-carbamic acid tert-butyl ester

Product 1

HCID 69287338(2S,3S)-2-amino-1-(2,4-dimethyl-benzylamino)-hexan-3-olYield 106.8%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A solution of (1S,2S)-(1-{[benzyloxycarbonyl-(2,4-dimethyl-benzyl)-amino]-methyl}-2-hydroxy-pentyl)-carbamic acid tert-butyl ester (600 mg, 1.2 mmol, see procedure 12a) in MeOH was charged with 5% Pd/C, Degussa style (120 mg), stirred under H2 (1 atm) for 12 h at RT, filtered, and concentrated in vacuo. The residue was dissolved in methylene chloride (6 mL) and the resultant solution was charged with trifluoroacetic acid (6 mL). The mixture was stirred for 3 h at RT and concentrated in vacuo. The residue was dissolved in benzene and the resultant solution was concentrated in vacuo; this procedure was repeated to provide (2S,3S)-2-amino-1-(2,4-dimethyl-benzylamino)-hexan-3-ol (321 mg). MS found: (M+H)+=251.4.

Workup

  1. filtrationfiltered
  2. concentrationconcentrated in vacuo
  3. dissolutionThe residue was dissolved in methylene chloride (6 mL)
  4. additionthe resultant solution was charged with trifluoroacetic acid (6 mL)
  5. stirringThe mixture was stirred for 3 h at RT
  6. concentrationconcentrated in vacuo
  7. dissolutionThe residue was dissolved in benzene
  8. concentrationthe resultant solution was concentrated in vacuo

Sources & evidence

ORD record
ord-8a5ac248821e42a887670ca5b163bcdd
Source dataset
uspto-grants-2007_06
Patent number
US07230133B2

Reaction notes

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