N,N,N',N'-Tetramethylethylenediamine → HCID 59770240, compound

HRID 2218754Notes

Reaction equation

HRID 2218754 reaction equation
[CH:1]1[CH:2]=[CH:3][N:4]2[CH2:10][CH2:9][C:8]3[CH:11]=[CH:12][CH:13]=[CH:14][C:7]=3[C:6](=O)[C:5]=12.[Li][CH:17]([Si](C)(C)C)[B:18]([O-:20])[O-:19].CN(CCN(C)C)C.[CH3:33][CH:34]1[CH2:39]CCN(C)[C:35]1([CH3:42])[CH3:41]>C1COCC1>[CH3:33][C:34]1([CH3:39])[C:35]([CH3:42])([CH3:41])[O:20][B:18](/[CH:17]=[C:6]2\[C:5]3[N:4]([CH:3]=[CH:2][CH:1]=3)[CH2:10][CH2:9][C:8]3[CH:11]=[CH:12][CH:13]=[CH:14][C:7]\2=3)[O:19]1

Participants

6

Reactant 4

HCID 8037N,N,N',N'-TetramethylethylenediamineHCID 12909379HCID 12909379, compoundHCID 187617721,2,2,3-TetramethylpiperidineHCID 178506889HCID 178506889, compound

Product 1

HCID 59770240HCID 59770240, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

Add one equiv of 5,6-dihydro-benzo[d]pyrrolo[1,2-a]azepin-11-one (prepared as described in Y. Girard, J. G. Atkinson, P. C. Belanger, J. J. Fuentes, J. Rokach, C. S. Rooney, D. C. Remy, C. A. Hunt J. Org. Chem. 1983, 48, 3220) in THF to a solution of 2.5 equiv of pinicol lithio(trimethylsilyl)methaneboronate (as described in D. S. Matteson, D. Majumder Organometallics 1983, 2, 230), 1 equiv TMEDA, 2.5 equiv of tetramethylpiperidine (TMP), and THF at −78° C. Allow the solution to warm to room temperature and stir for 3.5 h before quenching with excess water. Extract well with Et2O (4×). Dry (MgSO4) and concentrate under reduced pressure. Purify the crude residue by column chromatography (5% to 10% EtOAc:hexanes) to give pure E-isomer (45%) and

Workup

  1. customprepared
  2. customat −78° C
  3. custombefore quenching with excess water
  4. extractionExtract well with Et2O (4×)
  5. dry with materialDry (MgSO4)
  6. concentrationconcentrate under reduced pressure
  7. customPurify the crude residue by column chromatography (5% to 10% EtOAc:hexanes)
  8. customto give pure E-isomer (45%)

Sources & evidence

ORD record
ord-0bdea05f45ef4b3c92e4de97e53fec95
Source dataset
uspto-grants-2008_08
Patent number
US07411072B2

Reaction notes

Loading…