Isobutyraldehyde → HCID 5166296, compound

HRID 1928559Notes

Reaction equation

HRID 1928559 reaction equation
[C:1]1([C:7]#[CH:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH3:9][CH:10]([CH3:13])[CH:11]=O.[CH2:14]([NH:21][CH2:22][C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1)[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1>C1(C)C=CC=CC=1>[CH2:22]([N:21]([CH2:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)[CH:9]([CH:10]([CH3:13])[CH3:11])[C:8]#[C:7][C:1]1[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1)[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1

Participants

5

Reactant 3

HCID 6561IsobutyraldehydeHCID 7656DibenzylamineHCID 10821Phenylacetylene

Product 1

HCID 5166296HCID 5166296, compoundYield 85%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

In a dry, argon flushed 5 mL flask, equipped with a magnetic stirrer and a septum, CuBr (1.5 mg, 0.01 mmol, 5 mol %) and (R)(+)-FLiNAP (5.7 mg, 0.011 mmol, 5.5 mol %) were suspended in dry toluene (1 mL) and stirred for 30 min. Phenylacetylene (9) (21 mg, 0.2 mmol), 2-methylpropanal (7) (15 mg, 0.2 mmol) and dibenzylamine (8) (40 mg, 0.2 mmol) were then added. The reaction mixture was stirred at room temperature for 2 days. The crude product was concentrated under reduced pressure and purified by column chromatography on silica gel (95:5 pentane/ether) to yield the title compound 10 as an enantiomeric mixture. The enantiomers were subsequently separated using HPLC [(Chiralcel OD-H, 99% n-heptane/1% i-propanol, 0.2 mL/min): t, (min)=19.94 (−), 20.98 (+)]. The (−) isomer was isolated as an oil (60 mg, 85% yield, 87% ee).

Workup

  1. customIn a dry, argon flushed 5 mL flask
  2. customequipped with a magnetic stirrer
  3. stirringThe reaction mixture was stirred at room temperature for 2 days
  4. concentrationThe crude product was concentrated under reduced pressure
  5. custompurified by column chromatography on silica gel (95:5 pentane/ether)

Sources & evidence

ORD record
ord-1d7e4143a87d4456ada6ac6ec5291efc
Source dataset
uspto-grants-2012_05
Patent number
US08183378B2

Reaction notes

Loading…