N-Cbz-4-[(2,3-Dihydroxypropyloxy)phenyl]butylamine → 4-[(2,3-Dihydroxypropyloxy)phenyl]butylamine

HRID 217908Notes

Reaction equation

HRID 217908 reaction equation
C([NH:11][CH2:12][CH2:13][CH2:14][CH2:15][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=1[O:22][CH2:23][CH:24]([OH:27])[CH2:25][OH:26])(OCC1C=CC=CC=1)=O.[H][H]>CO.[Pd]>[OH:27][CH:24]([CH2:25][OH:26])[CH2:23][O:22][C:17]1[CH:18]=[CH:19][CH:20]=[CH:21][C:16]=1[CH2:15][CH2:14][CH2:13][CH2:12][NH2:11]

Participants

5

Reactant 2

HCID 11559794N-Cbz-4-[(2,3-Dihydroxypropyloxy)phenyl]butylamineHCID 178418361HCID 178418361, compound

Product 1

HCID 115288364-[(2,3-Dihydroxypropyloxy)phenyl]butylamineYield 67.2%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent2×

Procedure

Cbz-protected amine 31 (2.1 g, 5.6 mmol) was dissolved in methanol (50 mL) and Pd/C (0.46 g, 5% wet) was added in methanol (20 mL). The reaction mixture was stirred for 3 h at 1 atmosphere of hydrogen, then the solution was filtered through a pad of silica gel. The solvent was then evaporated to give free amine 32 (0.9 g, 66%). 1H NMR (300 MHz, DMSO-d6) δ 1.37 (m, 2H), 1.50 (m, 2H), 2.92 (m, 1H), 3.22-4.05 (br s, 4H), 3.43 (m, 2H), 3.93 (m, 1H), 6.82 (d, 2H), 7.07 (d, 2H).

Workup

  1. filtrationthe solution was filtered through a pad of silica gel
  2. customThe solvent was then evaporated

Sources & evidence

ORD record
ord-bbab7ef3cd7a455cb9f0d37a7eb5de6b
Source dataset
uspto-grants-2012_06
Patent number
US08198286B2

Reaction notes

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