Tetrahydrofuran → HCID 69154999, compound

HRID 2251957Notes

Reaction equation

HRID 2251957 reaction equation
CN(CCN(C)C)C.[C:9]([O:13][C:14](=[O:22])[NH:15][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)([CH3:12])([CH3:11])[CH3:10].[Li][CH:24]([CH2:26]C)[CH3:25].[NH4+].[Cl-:29].[CH2:30]1[CH2:34][O:33][CH2:32][CH2:31]1>>[C:9]([O:13][C:14](=[O:22])[NH:15][C:16]1[CH:17]=[CH:18][CH:19]=[CH:20][C:21]=1[CH:32]([C:31]1[CH:30]=[CH:34][CH:25]=[CH:24][C:26]=1[Cl:29])[OH:33])([CH3:12])([CH3:10])[CH3:11]

Participants

6

Reactant 5

HCID 8028TetrahydrofuranHCID 8037N,N,N',N'-TetramethylethylenediamineHCID 25517Ammonium ChlorideHCID 137930t-Butyl carbanilateHCID 178418400CID 53628100

Product 1

HCID 69154999HCID 69154999, compound

Procedure

Add TMEDA (8.3 mL, 55.0 mmol) to a solution of phenyl-carbamic acid tert-butyl ester (4.83 g, 25.0 mmol) in THF (50 mL) at −40° C. in a flame dried flask. After 5 min., add s-BuLi (43 mL, 55.0 mmol, 1.3 M in cyclohexane) dropwise over 10 min. Allow solution to warm to RT. After 30 min., add saturated aqueous NH4Cl solution (approx. 15 mL) and stir for 30 min. Concentrate, partition between 20% i-PrOH/CHCl3 and saturated aqueous NaHCO3 solution and separate. Wash organic layer with brine, dry over MgSO4, and concentrate. Purify the residue by flash chromatography on silica gel eluting with 0-20% ethyl acetate/hexanes to afford the title compound: TLC (10% ethyl acetate/hexanes) Rf=0.20.

Workup

  1. customdried flask
  2. waitAfter 30 min.
  3. concentrationConcentrate
  4. custompartition between 20% i-PrOH/CHCl3 and saturated aqueous NaHCO3 solution
  5. customseparate
  6. dry with materialWash organic layer with brine, dry over MgSO4
  7. concentrationconcentrate
  8. customPurify the residue by flash chromatography on silica gel eluting with 0-20% ethyl acetate/hexanes

Sources & evidence

ORD record
ord-0a7ceb3205714150913884206e55de7e
Source dataset
uspto-grants-2008_01
Patent number
US07320994B2

Reaction notes

Loading…