(R)-beta-aminophenethyl alcohol → HCID 54371180, compound

HRID 844044Notes

Reaction equation

HRID 844044 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]([O:7][C:8]2[N:16]=[CH:15][CH:14]=[CH:13][C:9]=2[C:10]([OH:12])=O)[CH:2]=1.[OH:17][CH2:18][C@H:19]([NH2:26])[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1>S(Cl)(Cl)=O.N1C=CC=CC=1.C(Cl)Cl>[OH:17][CH2:18][C@H:19]([NH:26][C:10](=[O:12])[C:9]1[CH:13]=[CH:14][CH:15]=[N:16][C:8]=1[O:7][C:3]1[CH:2]=[N:1][CH:6]=[CH:5][CH:4]=1)[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1

Participants

6

Reactant 2

HCID 2724025(R)-beta-aminophenethyl alcoholHCID 22032862HCID 22032862, compound

Product 1

HCID 54371180HCID 54371180, compound

Reagents, catalysts & solvents 3

HCID 1049PyridineSolventHCID 6344DichloromethaneSolventHCID 24386Thionyl ChlorideSolvent

Procedure

A solution of 2-(Pyridin-3-yloxy)-nicotinic acid (0.250 grams, 1.2 mmole) in thionyl chloride (10 ml) was heated to reflux. After 1 hour the reaction mixture was cooled to room temperature and concentrated under reduced pressure. The resulting residue was suspended in tetrahydrofuran (10 ml) and added dropwise to a solution of (R)-2-hydroxy-1-phenyl ethylamine (0.160 grams, 1.2 mmole) in pyridine (5 ml) at 0° C. After 30 minutes the mixture was warmed to room temperature, stirred at room temperature for 1 hour and concentrated to remove pyridine. The crude product was purified by chromatography on silica gel eluting with ethyl acetate to give a yellow oil. HRMS 336.1324; α=+63.9° 12.3 mg/ml in methylene chloride. 1H NMR (400 mhz, CDCl3) d 2.76 (bs, 1H), 3.95-4.02 (m, 2H), 5.31-5.36 (m, 1H), 7.16-7.40 (m, 1H), 8.19 (dd, J=2.1 Hz, 4.8 Hz, 1H), 8.48-8.61 (m, 4H).

Workup

  1. concentrationconcentrated under reduced pressure
  2. temperatureAfter 30 minutes the mixture was warmed to room temperature
  3. concentrationconcentrated
  4. customto remove pyridine
  5. customThe crude product was purified by chromatography on silica gel eluting with ethyl acetate
  6. customto give a yellow oil

Sources & evidence

ORD record
ord-a0ba32b0576541eab98c9023d7cd4a5d
Source dataset
uspto-grants-2002_04
Patent number
US06380218B1

Reaction notes

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