(2R)-3-(benzyloxy)-2-[(3-nitroquinolin-4-yl)amino]propan-1-ol → (2R)-2-[(3-aminoquinolin-4-yl)amino]-3-(benzyloxy)propan-1-ol

HRID 1663452Notes

Reaction equation

HRID 1663452 reaction equation
[CH2:1]([O:8][CH2:9][C@H:10]([NH:13][C:14]1[C:23]2[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=2)[N:17]=[CH:16][C:15]=1[N+:24]([O-])=O)[CH2:11][OH:12])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1>C(#N)C.C(O)(C)C.[Pt]>[NH2:24][C:15]1[CH:16]=[N:17][C:18]2[C:23]([C:14]=1[NH:13][C@@H:10]([CH2:9][O:8][CH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1)[CH2:11][OH:12])=[CH:22][CH:21]=[CH:20][CH:19]=2

Participants

5

Reactant 1

HCID 59828596(2R)-3-(benzyloxy)-2-[(3-nitroquinolin-4-yl)amino]propan-1-ol

Product 1

HCID 67435482(2R)-2-[(3-aminoquinolin-4-yl)amino]-3-(benzyloxy)propan-1-olYield 99.5%

Reagents, catalysts & solvents 3

HCID 23939PlatinumCatalystHCID 3776IsopropanolSolventHCID 6342AcetonitrileSolvent

Procedure

(2R)-3-(benzyloxy)-2-[(3-nitroquinolin-4-yl)amino]propan-1-ol (31 g, 87 mmol) was dissolved in a mixture of acetonitrile (810 mL) and isopropyl alcohol (90 mL) and the solution was placed in a pressure bottle. Platinum on carbon (5%, 3.1 g) was then added and the reaction mixture was shaken under H2 at 48 PSI (3.3×105 Pa). After 2 hours, the reaction mixture was filtered through a pad of CELITE filter agent. The pad was rinsed with acetonitrile and the combined filtrates were concentrated under reduced pressure to give (2R)-2-[(3-aminoquinolin-4-yl)amino]-3-(benzyloxy)propan-1-ol (28 g) as an orange oil.

Workup

  1. filtrationthe reaction mixture was filtered through a pad of CELITE
  2. filtrationfilter agent
  3. washThe pad was rinsed with acetonitrile
  4. concentrationthe combined filtrates were concentrated under reduced pressure

Sources & evidence

ORD record
ord-167df97bdfea47459da550de90dded17
Source dataset
uspto-grants-2011_10
Patent number
US08034938B2

Reaction notes

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