{4-[4-((2R)-2,3-Dihydroxypropylamino)phenyl]butyl}carbamic acid benzyl ester → 4-[4-((2R)-2,3-Dihydroxypropylamino)phenyl]butylamine

HRID 254390Notes

Reaction equation

HRID 254390 reaction equation
C(OC(=O)[NH:10][CH2:11][CH2:12][CH2:13][CH2:14][C:15]1[CH:20]=[CH:19][C:18]([NH:21][CH2:22][C@@H:23]([OH:26])[CH2:24][OH:25])=[CH:17][CH:16]=1)C1C=CC=CC=1>CO.[Pd]>[OH:26][C@@H:23]([CH2:24][OH:25])[CH2:22][NH:21][C:18]1[CH:19]=[CH:20][C:15]([CH2:14][CH2:13][CH2:12][CH2:11][NH2:10])=[CH:16][CH:17]=1

Participants

4

Reactant 1

HCID 58664830{4-[4-((2R)-2,3-Dihydroxypropylamino)phenyl]butyl}carbamic acid benzyl ester

Product 1

HCID 586648454-[4-((2R)-2,3-Dihydroxypropylamino)phenyl]butylamineYield 90%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

The protected amine 700 (0.29 g, 0.77 mmol) was stirred at room temperature for 6 h in methanol (20 mL) with 10% Pd/C (129 mg, 50% wet) under hydrogen (1 atm). The catalyst was filtered off and the solvent was removed under reduced pressure to give amine 710 (0.165 g, 90%) as a clear oil. 1H NMR (300 MHz, CD3OD) δ 1.56 (m, 4H), 2.51 (t, 2H), 2.71 (t, 2H), 3.02 (m, 1H), 3.27 (m, 1H), 3.30 (m, 2H), 3.56 (m, 2H), 3.80 (m, 1H), 6.60 (d, 2H), 6.95 (d, 2H). m/z (ESI) 239 [C13H22N2O2+H]+.

Workup

  1. filtrationThe catalyst was filtered off
  2. customthe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-33c6b6dc343b46dda78381199a5954cc
Source dataset
uspto-grants-2011_01
Patent number
US07875619B2

Reaction notes

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