Boron tribromide → HCID 68705199, compound

HRID 2376490Notes

Reaction equation

HRID 2376490 reaction equation
[CH:1]([C:4]1[CH:9]=[CH:8][C:7]([C@@H:10]2[C:14]3[C:15]([CH3:30])=[C:16]([NH:22][C:23](=[O:29])[CH2:24][C:25]([CH3:28])([CH3:27])[CH3:26])[C:17]([CH3:21])=[C:18]([O:19]C)[C:13]=3[O:12][CH2:11]2)=[CH:6][CH:5]=1)([CH3:3])[CH3:2].B(Br)(Br)Br.C(=O)([O-])O.[Na+]>ClCCl>[OH:19][C:18]1[C:13]2[O:12][CH2:11][C@H:10]([C:7]3[CH:6]=[CH:5][C:4]([CH:1]([CH3:2])[CH3:3])=[CH:9][CH:8]=3)[C:14]=2[C:15]([CH3:30])=[C:16]([NH:22][C:23](=[O:29])[CH2:24][C:25]([CH3:28])([CH3:27])[CH3:26])[C:17]=1[CH3:21]

Participants

5

Reactant 3

HCID 25134Boron tribromideHCID 516892Sodium BicarbonateHCID 68705577HCID 68705577, compound

Product 1

HCID 68705199HCID 68705199, compoundYield 78.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of (+)-N-((3R)-3-(4-isopropylphenyl)-7-methoxy-4,6-dimethyl-2,3-dihydro-1-benzofuran-5-yl)-3,3-dimethylbutanamide (500 mg, 1.22 mmol) obtained in Example 52 in dichloromethane (20 mL) was added dropwise at −78° C. under an argon atmosphere boron tribromide (1.0 M dichloromethane solution, 3.0 mL, 3.0 mmol). The reaction solution was warmed to room temperature, added to an aqueous saturated sodium hydrogen carbonate solution, and extracted with ethyl acetate. The combined organic layers were washed with saturated brine, dried over sodium sulfate, filtered, and then concentrated under reduced pressure. The obtained residue was purified by silica gel column chromatography (ethyl acetate:hexane=1:2) to synthesize 378 mg (yield: 78%) of the title compound. Melting point: 202-203° C. (ethyl acetate-hexane). [α]D20=+79.00 (c=0.49, chloroform).

Workup

  1. extractionextracted with ethyl acetate
  2. washThe combined organic layers were washed with saturated brine
  3. dry with materialdried over sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure
  6. customThe obtained residue was purified by silica gel column chromatography (ethyl acetate:hexane=1:2)

Sources & evidence

ORD record
ord-7820b7ea5c454ab699e149aa17e97178
Source dataset
uspto-grants-2008_12
Patent number
US07465815B2

Reaction notes

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