Boron tribromide → HCID 86615322, compound

HRID 1362491Notes

Reaction equation

HRID 1362491 reaction equation
[F:1][C:2]1[C:3]([O:32][CH3:33])=[C:4]([C@H:8]([CH2:30][CH3:31])[CH2:9][C@@:10]([C:26]([F:29])([F:28])[F:27])([OH:25])[CH:11]=NC2C=C(F)C=C3C=2C=CC(C)=N3)[CH:5]=[CH:6][CH:7]=1.B(Br)(Br)Br.C([O-])(O)=[O:39].[Na+]>C(Cl)Cl>[F:1][C:2]1[C:3]([O:32][CH3:33])=[C:4]([C@H:8]([CH2:30][CH3:31])[CH2:9][C@:10]([OH:25])([C:26]([F:27])([F:28])[F:29])[CH:11]=[O:39])[CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 25134Boron tribromideHCID 516892Sodium BicarbonateHCID 66969271HCID 66969271, compound

Product 1

HCID 86615322HCID 86615322, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
-40 °C

Procedure

The suspension is filtered through Celite, the filter bed being rinsed thoroughly with ethyl acetate. The phases of the filtrate are separated and extraction is carried out again with ethyl acetate. The extracts are dried over sodium sulphate and the solvent is removed in vacuo to give 205 mg of (2R,4R)-4-(3-fluoro-2-methoxyphenyl)-1-[(7-fluoro-2-methylquinolin-5-yl)imino]-2-(trifluoromethyl)-hexan-2-ol as a crude product. The crude imine is dissolved in 18 ml of CH2Cl2 and the solution is cooled to −40° C. 3.4 ml (3.4 mmol) of a 1 M BBr3 solution in dichloromethane are added slowly dropwise over 5 minutes and the mixture is allowed to warm to 0° C. over 1 hour, and after 30 minutes at 0° C. is poured onto a mixture of saturated NaHCO3 and ice. It is extracted repeatedly with ethyl acetate and the extracts are washed with saturated NaCl solution and dried over Na2SO4. Purification by column chromatography on silica gel (150 ml) with ethyl acetate affords 37 mg of product (analytical HPLC: Rt=9.2 min (Chiralcel OD 5μ, 250×4.6 mm, hexane/ethanol 10%, 1 ml/min flow rate) as the (−)-enantiomer.

Workup

  1. temperatureto warm to 0° C. over 1 hour
  2. extractionIt is extracted repeatedly with ethyl acetate
  3. washthe extracts are washed with saturated NaCl solution
  4. dry with materialdried over Na2SO4
  5. customPurification by column chromatography on silica gel (150 ml) with ethyl acetate

Sources & evidence

ORD record
ord-6cf3e5905d354bde8b4c47e420f30203
Source dataset
uspto-grants-2011_02
Patent number
US07880042B2

Reaction notes

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