Borane → HCID 21107220, compound

HRID 2377319Notes

Reaction equation

HRID 2377319 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]2[C:9](=[C:10]([CH2:12][N:13]([CH:16]3[CH2:18][CH2:17]3)[CH:14]=O)[CH:11]=1)[O:8][C:7]([CH3:20])([CH3:19])[CH2:6][C:5]2([CH3:22])[CH3:21].B>O1CCCC1>[Br:1][C:2]1[CH:3]=[C:4]2[C:9](=[C:10]([CH2:12][N:13]([CH:16]3[CH2:18][CH2:17]3)[CH3:14])[CH:11]=1)[O:8][C:7]([CH3:20])([CH3:19])[CH2:6][C:5]2([CH3:22])[CH3:21]

Participants

4

Reactant 2

HCID 6331BoraneHCID 21107219HCID 21107219, compound2×

Product 1

HCID 21107220HCID 21107220, compoundYield 110%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of 6-bromo-8-[(cyclopropyl-formyl-amino)-methyl]-2,2,4,4-tetramethyl-chroman (Intermediate 8, 1.46 g, 4.0 mmol) in anhydrous tetrahydrofuran (30 mL) was treated with a 2M solution of borane:methylsulfide complex in tetrahydrofuran (5 mL, 10 mmol) and the resulting reaction mixture was refluxed for 2 h. It was then cooled in an ice bath, quenched cautiously with saturated aqueous sodium carbonate solution and extracted with diethyl ether. The organic phase was washed with water and brine, dried over anhydrous magnesium sulfate, filtered and evaporated in vacuo to afford the title product as a white solid (1.55 g, 100%).

Workup

  1. temperaturewas refluxed for 2 h
  2. temperatureIt was then cooled in an ice bath
  3. customquenched cautiously with saturated aqueous sodium carbonate solution
  4. extractionextracted with diethyl ether
  5. washThe organic phase was washed with water and brine
  6. dry with materialdried over anhydrous magnesium sulfate
  7. filtrationfiltered
  8. customevaporated in vacuo

Sources & evidence

ORD record
ord-08d745948dac429399531ddda65ab0d9
Source dataset
uspto-grants-2008_12
Patent number
US07468391B2

Reaction notes

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