Diethanolamine → (R)-2-Bromo-1-(6-methoxy-[1,5]-naphthyridin-4-yl)ethanol

HRID 638996Notes

Reaction equation

HRID 638996 reaction equation
[Br:1][CH2:2][C:3]([C:5]1[C:14]2[C:9](=[CH:10][CH:11]=[C:12]([O:15][CH3:16])[N:13]=2)[N:8]=[CH:7][CH:6]=1)=[O:4].B(Cl)([C@@H]1[C@@H](C)[C@H]2C(C)(C)[C@@H](C2)C1)[C@@H]1[C@@H](C)[C@@H]2C(C)(C)[C@@H](C2)C1.N(CCO)CCO>C1(C)C=CC=CC=1>[Br:1][CH2:2][C@@H:3]([C:5]1[C:14]2[C:9](=[CH:10][CH:11]=[C:12]([O:15][CH3:16])[N:13]=2)[N:8]=[CH:7][CH:6]=1)[OH:4]

Participants

5

Reactant 3

HCID 8113DiethanolamineHCID 21948949Ethanone, 2-bromo-1-(6-methoxy-1,5-naphthyridin-4-yl)-HCID 91873398(+)-b-Chlorodiisopinocamphenylborane

Product 1

HCID 23400264(R)-2-Bromo-1-(6-methoxy-[1,5]-naphthyridin-4-yl)ethanolYield 73%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

Bromomethyl-(6-methoxy-[1,5]-naphthyridin-4-yl)-ketone (6.6 g, 0.023 mol) in toluene was treated with (+)-B-chlorodiisopinocamphenylborane ((+)-DIP-chloride) (12 g, 0.037 mol) and stirred overnight, then diethanolamine (15 g, 0.14 mol) added and the mixture stirred for 3 hours, filtered and evaporated. Chromatography on silica gel (ethyl acetate-hexane) gave a white solid (4.73 g, 73%).

Workup

  1. stirringthe mixture stirred for 3 hours
  2. filtrationfiltered
  3. customevaporated

Sources & evidence

ORD record
ord-a15e3a634802450793e83e08d02bbee7
Source dataset
uspto-grants-2010_04
Patent number
US07691850B2

Reaction notes

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