Selectfluor → HCID 9947224, compound

HRID 992845Notes

Reaction equation

HRID 992845 reaction equation
[CH3:1][CH:2]([C:22](=[O:25])[CH2:23][CH3:24])[C:3]([O:5][CH2:6][C:7]1[C:12]([CH:13]([CH3:15])[CH3:14])=[CH:11][C:10]([CH:16]([CH3:18])[CH3:17])=[CH:9][C:8]=1[CH:19]([CH3:21])[CH3:20])=[O:4].[B-](F)(F)(F)[F:27].[B-](F)(F)(F)F.C1[N+]2(CCl)CC[N+](F)(CC2)C1>O>[F:27][C:2]([CH3:1])([C:22](=[O:25])[CH2:23][CH3:24])[C:3]([O:5][CH2:6][C:7]1[C:12]([CH:13]([CH3:14])[CH3:15])=[CH:11][C:10]([CH:16]([CH3:17])[CH3:18])=[CH:9][C:8]=1[CH:19]([CH3:21])[CH3:20])=[O:4]

Participants

4

Reactant 2

HCID 2724933SelectfluorHCID 11198798HCID 11198798, compound

Product 1

HCID 9947224HCID 9947224, compoundYield 89.2%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
0 °C

Procedure

At 0° C., 444 mg of 2,4,6-triisopropylbenzyl 2-methyl-3-oxopentanoate (1.28 mmol) are dissolved in 10 ml of F-TEDA (0.145 M in MeCN, 1.45 mmol). After equilibration for 10 minutes, 1.28 ml of catalyst C7 (0.05 M in MeCN, 0.064 mmol, 5 mol %) are added dropwise and the resulting cloudy, lemon-yellow solution is stirred at 0° C. for 25 h. The reaction mixture is taken up in water and TBME, and the organic phase is separated off, washed twice with saturated aqueous NaCl solution and concentrated in an RE. Purification of the crude product by liquid chromatography (TBME/hexane 1:25) affords 416 mg (89%) of 2,4,6-triisopropylbenzyl 2-fluoro-2-methyl-3-oxopentanoate as colourless oil with an ee of 85.6%.

Workup

  1. customTBME, and the organic phase is separated off
  2. washwashed twice with saturated aqueous NaCl solution
  3. concentrationconcentrated in an RE
  4. customPurification of the crude product by liquid chromatography (TBME/hexane 1:25)

Sources & evidence

ORD record
ord-67c4dccdc7a041a5af0a156b11274c6c
Source dataset
uspto-grants-2002_10
Patent number
US06472345B2

Reaction notes

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