Diisopropylamine → HCID 86690101, compound

HRID 520388Notes

Reaction equation

HRID 520388 reaction equation
[Li+].CC([N-]C(C)C)C.C(NC(C)C)(C)C.C([Li])CCC.[CH:21]1([C:24]([O:26][C:27]([CH3:30])([CH3:29])[CH3:28])=[O:25])[CH2:23][CH2:22]1.[F:31][C:32]1([F:39])[CH2:37][CH2:36][C:35](=[O:38])[CH2:34][CH2:33]1>C1COCC1>[F:31][C:32]1([F:39])[CH2:37][CH2:36][C:35]([C:21]2([C:24]([O:26][C:27]([CH3:30])([CH3:29])[CH3:28])=[O:25])[CH2:23][CH2:22]2)([OH:38])[CH2:34][CH2:33]1

Participants

7

Reactant 5

HCID 7912DiisopropylamineHCID 2724682Lithium diisopropylamideHCID 13676038tert-Butyl cyclopropanecarboxylateHCID 157890924,4-DifluorocyclohexanoneHCID 178418339Butyllithium

Product 1

HCID 86690101HCID 86690101, compoundYield 49.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent3×

Conditions

Temperature
-78 °C

Procedure

A solution of LDA prepared from diisopropylamine (304 mg, 3.00 mmol) and butyllithium (1.20 mL, 3.00 mmol) in THF was added to a cold (−78° C.) solution of tert-butyl cyclopropanecarboxylate (427 mg, 3.00 mmol) in THF (2 mL), and the mixture was stirred at −78° C. for 1 h. A solution of 4,4-difluorocyclohexanone (268 mg, 2 mmol) in THF (0.5 mL) was added dropwise and the mixture was stirred at −78° C. for 2 h and allowed to warm to rt overnight. The crude product was purified by silica gel FCC (DCM) to afford tert-butyl 1-(4,4-difluoro-1-hydroxycyclohexyl)cyclopropanecarboxylate as a clear oil (0.273 g). 1H NMR (500 MHz, CDCl3) δ ppm 2.12-2.30 (2H, m), 1.79-1.96 (4H, m), 1.48-1.53 (2H, m), 1.41-1.47 (9H, m), 1.21-1.34 (1H, m), 1.11-1.17 (2H, m), 0.90-0.97 (2H, m).

Workup

  1. stirringthe mixture was stirred at −78° C. for 2 h
  2. temperatureto warm to rt overnight
  3. customThe crude product was purified by silica gel FCC (DCM)

Sources & evidence

ORD record
ord-366ab1aebcae4533a3a806aa5dd2c306
Source dataset
uspto-grants-2016_05
Patent number
US09326973B2

Reaction notes

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