Tetrahydrofuran → (R)-7-(1-methoxypropan-2-yloxy)-2-methylquinoline

HRID 338967

Reaction equation

HRID 338967 reaction equation
[CH3:1][C:2]1[CH:11]=[CH:10][C:9]2[C:4](=[CH:5][C:6]([OH:12])=[CH:7][CH:8]=2)[N:3]=1.[O:13]1[CH2:17][CH2:16][CH2:15][CH2:14]1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C(OCC)=O)=NC(OCC)=O.COC[C@@H](O)C>O>[CH3:17][O:13][CH2:14][C@H:15]([O:12][C:6]1[CH:5]=[C:4]2[C:9]([CH:10]=[CH:11][C:2]([CH3:1])=[N:3]2)=[CH:8][CH:7]=1)[CH3:16]

Participants

7

Reactant 5

HCID 8028TetrahydrofuranHCID 11776TriphenylphosphineHCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 6993459(2S)-1-methoxypropan-2-olHCID 1354519692-Methylquinolin-7-ol

Product 1

HCID 86707484(R)-7-(1-methoxypropan-2-yloxy)-2-methylquinolineYield 73.2%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a solution of 2-methylquinolin-7-ol (0.20 g, 1.3 mmol) in tetrahydrofuran (1.1 mL, 1.3 mmol) was added triphenylphosphine (0.82 g, 3.1 mmol), diethyl azodicarboxylate (0.32 mL, 2.0 mmol), and (S)-1-methoxypropan-2-ol (0.16 mL, 1.6 mmol) and the resultant mixture allowed to stir at ambient temperature for 24 hours. The reaction mixture was diluted with water (10 mL) and extracted with dichloromethane (2×20 mL). The combined organic extracts dried over sodium sulfate, filtered and concentrated under reduced pressure. Purification by reverse phase chromatography on C18 (0-80% acetonitrile/water) afforded the title compound (0.22 g, 66%).

Workup

  1. extractionextracted with dichloromethane (2×20 mL)
  2. dry with materialThe combined organic extracts dried over sodium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated under reduced pressure
  5. customPurification by reverse phase chromatography on C18 (0-80% acetonitrile/water)

Sources & evidence

ORD record
ord-2c8d10cbb8e1476399fa16159c03c6e6
Source dataset
uspto-grants-2014_11
Patent number
US08889704B2

Linked notes

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