2-Amino-1-(4-hydroxyphenyl)ethanol hydrochloride → HCID 178454272, compound

HRID 452288Notes

Reaction equation

HRID 452288 reaction equation
[CH:1]1[C:6]([CH:7]([OH:10])[CH2:8][NH2:9])=[CH:5][CH:4]=[C:3]([OH:11])[CH:2]=1.Cl.[C:13]([NH:20][C:21](N1C=CC=N1)=[N:22][C:23]([O:25][C:26]([CH3:29])([CH3:28])[CH3:27])=[O:24])([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14]>CN(C=O)C>[OH:10][CH:7]([C:6]1[CH:5]=[CH:4][C:3]([OH:11])=[CH:2][CH:1]=1)[CH2:8][NH:9][C:21]([NH:20][C:13]([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14])=[N:22][C:23]([O:25][C:26]([CH3:29])([CH3:28])[CH3:27])=[O:24]

Participants

4

Reactant 2

HCID 1024842-Amino-1-(4-hydroxyphenyl)ethanol hydrochlorideHCID 4428040N,N'-Bis(tert-butoxycarbonyl)-1H-pyrazole-1-carboxamidine

Product 1

HCID 178454272HCID 178454272, compoundYield 73.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of (+/−)-octopamine hydrochloride (500 mg, 2.89 mmol) and N,N′-bis(Boc)-1H-pyrazole-1-carboxamidine (1.13 g, 3.60 mmol) in DMF (10 mL) was stirred for 1 h at ambient temperatures. The reaction mixture was concentrated, and the residue was dissolved in EtOAc (60 mL). The solution was washed with 1 N KHSO4 (2×30 mL) and 5% Na2CO3 (30 mL). The organic layer was dried (Na2SO4), concentrated, and purified by flash chromatography (EtOAc/hexane 30/70→50/50) to yield the title compound as a colorless solid (836 mg, 73%). 1H NMR (CDCl3, 600 MHz): δ 11.45 (bs, 1H), 8.76 (s, 1H), 7.15 (d, J=8.4 Hz, 2H), 6.77 (d, J=8.4 Hz, 2H), 6.52 (bs, 1H), 4.81-4.78 (m, 1H), 3.66-3.50 (m, 2H), 1.51 (s, 9H), 1.49 (s, 9H); 13C NMR (CDCl3, 150 MHz): δ 162.86, 157.52, 156.04, 153.19, 133.52, 127.34, 115.65, 83.83, 80.07, 73.95, 49.49, 28.41, 28.26. MS (ESI): 396.4 (M+H, 100), 340.3 (M+H−tBu, 15).

Workup

  1. concentrationThe reaction mixture was concentrated
  2. dissolutionthe residue was dissolved in EtOAc (60 mL)
  3. washThe solution was washed with 1 N KHSO4 (2×30 mL) and 5% Na2CO3 (30 mL)
  4. dry with materialThe organic layer was dried (Na2SO4)
  5. concentrationconcentrated
  6. custompurified by flash chromatography (EtOAc/hexane 30/70→50/50)

Sources & evidence

ORD record
ord-e5c7c486aebe4a9c852e6e1831d2767d
Source dataset
uspto-grants-2013_07
Patent number
US08491868B2

Reaction notes

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