Acetone → HCID 16123135, compound

HRID 219311Notes

Reaction equation

HRID 219311 reaction equation
[CH3:1][C:2]([CH3:4])=[O:3].[Br:5][C:6]1[CH:13]=[CH:12][C:9]([CH:10]=[O:11])=[CH:8][CH:7]=1>N1CCC[C@H]1C(O)=O.CN(C=O)C>[OH:11][CH:10]([C:9]1[CH:12]=[CH:13][C:6]([Br:5])=[CH:7][CH:8]=1)[CH2:1][C:2](=[O:3])[CH3:4]

Participants

5

Reactant 2

HCID 180AcetoneHCID 707414-Bromobenzaldehyde

Product 1

HCID 16123135HCID 16123135, compound

Reagents, catalysts & solvents 2

HCID 145742L-ProlineCatalystHCID 6228DimethylformamideSolvent

Procedure

A stirred solution of catalyst 35 (0.01 g, 0.011 mmol) in dry DMF (0.785 mL) and acetone (0.392 mL, 2.72 mmol) was treated with 4-bromobenzaldehyde (0.0072 g, 0.04 mmol), stirred at room temperature for 68 h and Resin 35 was filtered off. The mixture was treated with Et2O and washed twice with water Et2O phase was dried and concentrated The product was analyzed by the 1H NMR spectroscopy of the crude 1H NMR spectroscopy of the crude showed a 70% conversion by measuring the CHOH peak of the aldol product at 5.12 ppm vs the CHO peak of the p-bromobenzaldehyde at 9.90 ppm 1H NMR (CDCl3, 400 MHz): δ=2.20 (s, 3H), 2.82 (m, 2H), 5.12 (m, 1H), 3.58-3.69 (m, 1H), 4.11-4.17 (m, 1H), 4.29-4.35 (m, 2H), 7.24-47 (m, 4H). Moreover, examination of the aldol product by chiral HPLC using a Chiralpak AS Daicel (i-PrOH/hexane 15/85), UV 280 nm, flow rate 1.0 mL/min, tRminor 8.950 min and tRmajor 10.143 min showed the presence of one single peak at 8.950 min retention time.

Workup

  1. filtrationResin 35 was filtered off
  2. additionThe mixture was treated with Et2O
  3. washwashed twice with water Et2O phase
  4. customwas dried
  5. concentrationconcentrated The product
  6. customAS Daicel (i-PrOH/hexane 15/85), UV 280 nm, flow rate 1.0 mL/min, tRminor 8.950 min and tRmajor 10.143 min
  7. customat 8.950 min

Sources & evidence

ORD record
ord-c98fbe3e9b1541dfba5a267ae3bbc1a1
Source dataset
uspto-grants-2012_06
Patent number
US08198364B2

Reaction notes

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