Dimethylamine → HCID 9885379, compound

HRID 850339Notes

Reaction equation

HRID 850339 reaction equation
[C:1]([O:5][C:6](=[O:24])[CH:7]([C:9]1[CH:14]=[C:13]([C:15]([CH3:18])([CH3:17])[CH3:16])[C:12]([OH:19])=[C:11]([C:20]([CH3:23])([CH3:22])[CH3:21])[CH:10]=1)Br)([CH3:4])([CH3:3])[CH3:2].C1COCC1.[CH3:30][NH:31][CH3:32]>>[C:1]([O:5][C:6](=[O:24])[CH:7]([C:9]1[CH:14]=[C:13]([C:15]([CH3:18])([CH3:17])[CH3:16])[C:12]([OH:19])=[C:11]([C:20]([CH3:23])([CH3:22])[CH3:21])[CH:10]=1)[N:31]([CH3:32])[CH3:30])([CH3:4])([CH3:3])[CH3:2]

Participants

4

Reactant 3

HCID 674DimethylamineHCID 8028TetrahydrofuranHCID 54161484HCID 54161484, compound

Product 1

HCID 9885379HCID 9885379, compound

Procedure

To a solution of Intermediate 19 (0.8654 g, 2.17 mmol) in 8 mL, THF was bubbled in dimethylamine. The reaction was stirred at ambient temperature overnight. The solvent was removed in vacuo. The residue was taken up in ethyl acetate, washed with brine, dried over MgSO4, and concentrated. The crude product was chromatographed on silica eluting with 5% to 20% EtOAc/hex. The resulting yellow oil crystallized to a yellow solid under high vacuum overnight

Workup

  1. customThe solvent was removed in vacuo
  2. washwashed with brine
  3. dry with materialdried over MgSO4
  4. concentrationconcentrated
  5. customThe crude product was chromatographed on silica eluting with 5% to 20% EtOAc/hex
  6. customThe resulting yellow oil crystallized to a yellow solid under high vacuum overnight

Sources & evidence

ORD record
ord-a6c1b8bbfb4147ad94fa3403341dfbcd
Source dataset
uspto-grants-2000_01
Patent number
US06017918

Reaction notes

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