Diisopropylamine → HCID 19594890, compound

HRID 612604Notes

Reaction equation

HRID 612604 reaction equation
[Li+].CC([N-][CH:6]([CH3:8])[CH3:7])C.[CH2:9]([Li])[CH2:10][CH2:11]C.C(NC(C)C)(C)C.C(N(CC)[C:24]([C:26]1[C:27]([C:36]2[CH:41]=[CH:40][C:39]([O:42][CH3:43])=[CH:38][C:37]=2[O:44][CH3:45])=C(OC(C)C)C=C[CH:31]=1)=[O:25])C.[O:48]1CCCC1>>[CH:10]([O:48][C:7]1[CH:6]=[CH:8][CH:31]=[C:26]2[C:27]=1[C:36]1[C:37]([O:44][CH3:45])=[CH:38][C:39]([O:42][CH3:43])=[CH:40][C:41]=1[C:24]2=[O:25])([CH3:11])[CH3:9]

Participants

6

Reactant 5

HCID 7912DiisopropylamineHCID 8028Tetrahydrofuran2×HCID 2724682Lithium diisopropylamideHCID 19594913HCID 19594913, compoundHCID 178418339Butyllithium

Product 1

HCID 19594890HCID 19594890, compoundYield 83%

Conditions

Temperature
0 °C

Procedure

Similar to Example 7C prepare the LDA reagent by adding dropwise n-butyl lithium (8.2 mL, 21 mmole of 2.5 M) to diisopropyl amine (2.0 g, 2.8 mL/d=0.722, 20.3 mmol) at -50° C. in 50 mL tetrahydrofuran (THF) under argon. Allow reaction to warm to 0° C. then dropwise add N,N-diethyl-6-isopropoxy-2',4'-dimethoxy-biphenyl-2-carboxamide (3.0 g, 8.1 mmole) in 50 mL THF. Allow reaction to further warm to room temperature and stir overnight. Continue procedure from Example 7C to obtain 2.0 g (6.7 mmole, 83%) of the title compound. (EtOAc/hexane 4:6, Rf=0.50)

Workup

  1. customreaction
  2. customreaction
  3. temperatureto further warm to room temperature

Sources & evidence

ORD record
ord-6f1d0c8649ea46a58c3e4d774711d236
Source dataset
uspto-grants-1999_12
Patent number
US06004959

Reaction notes

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