Borane → HCID 4717570, compound

HRID 1725237Notes

Reaction equation

HRID 1725237 reaction equation
[CH2:1]([NH:8][C:9](=O)[C:10]1[CH:15]=[CH:14][CH:13]=[C:12]([O:16][CH3:17])[C:11]=1[O:18][CH3:19])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH3:7].B>C1COCC1.C(OCC)C>[CH3:19][O:18][C:11]1[C:12]([O:16][CH3:17])=[CH:13][CH:14]=[CH:15][C:10]=1[CH2:9][NH:8][CH2:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH3:7]

Participants

5

Reactant 2

HCID 6331BoraneHCID 23132707HCID 23132707, compound

Product 1

HCID 4717570HCID 4717570, compoundYield 55.2%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent

Procedure

N-Heptyl-2,3-dimethoxybenzamide (6.47 g, 23.2 mmol) was dissolved in freshly distilled THF (230 mL) and cooled in an ice bath under an argon atmosphere. Borane (29 mL of a 2 M solution of the dimethylsulfide complex in diethyl ether) was added and the ice bath was removed after 15 minutes. The reaction mixture was refluxed overnight and was then allowed to cool to room temperature. The reaction was quenched by careful addition of 10% HCl (11 mL) and the mixture was stirred for four hours and then concentrated in vacuo. The residue was taken up in ethyl acetate (300 mL) and washed with aqueous 2 M K2CO3 (3×100 mL) and brine (100 mL), dried over Na2SO4, and concentrated in vacuo. Purification on silica gel (160 g) with ethyl acetate (33-100% gradient) in heptane and finally 5% ethanol in ethyl acetate as the eluent yielded 3.40 g (55%) of a light yellow oil.

Workup

  1. temperaturecooled in an ice bath under an argon atmosphere
  2. customthe ice bath was removed after 15 minutes
  3. temperatureThe reaction mixture was refluxed overnight
  4. customThe reaction was quenched by careful addition of 10% HCl (11 mL)
  5. concentrationconcentrated in vacuo
  6. washwashed with aqueous 2 M K2CO3 (3×100 mL) and brine (100 mL)
  7. dry with materialdried over Na2SO4
  8. concentrationconcentrated in vacuo
  9. customPurification on silica gel (160 g) with ethyl acetate (33-100% gradient) in heptane and finally 5% ethanol in ethyl acetate as the eluent

Sources & evidence

ORD record
ord-45948640f3064b80b70b414cbfa96297
Source dataset
uspto-grants-2009_02
Patent number
US07488844B2

Reaction notes

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