3-Methylbutanal → HCID 59853584, compound

HRID 730528Notes

Reaction equation

HRID 730528 reaction equation
[CH2:1]([O:4][C:5]([C:7]1[N:8]([NH2:13])[CH:9]=[C:10]([F:12])[CH:11]=1)=[O:6])[CH:2]=[CH2:3].[CH:14](=O)[CH2:15][CH:16]([CH3:18])[CH3:17].C([BH3-])#N.[Na+]>CO>[CH2:1]([O:4][C:5]([C:7]1[N:8]([NH:13][CH2:14][CH2:15][CH:16]([CH3:18])[CH3:17])[CH:9]=[C:10]([F:12])[CH:11]=1)=[O:6])[CH:2]=[CH2:3]

Participants

5

Reactant 3

HCID 115523-MethylbutanalHCID 5003444Sodium cyanoborohydrideHCID 59853575HCID 59853575, compound

Product 1

HCID 59853584HCID 59853584, compoundYield 38.2%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
25 °C

Procedure

To a solution of 1-amino-4-fluoro-1H-pyrrole-2-carboxylic acid allyl ester (Example 14f, 0.5 g, 2.717 mmol) in methanol (20 mL) were added isovaleraldehyde (0.257 g, 2.988 mmol) and sodium cyanoborohydride (0.256 g, 4.075 mmol). The mixture was stirred for 20 h at 25° C. The solvent was removed in vacuo and the crude product was purified by flash column chromatography (Merck silica gel 60, 40-63 μm, 20% ethyl acetate in hexanes) to afford the desired product, 4-fluoro-1-(3-methyl-butylamino)-1H-pyrrole-2-carboxylic acid allyl ester (0.264 g, 1.039 mmol, 38.2% yield) as a yellow oil. 1H NMR (400 MHz, CDCl3) δ: 0.91 (3H, s), 0.93 (3H, s), 1.38-1.45 (2H, m), 1.63-1.80 (1H, m), 3.00-3.05 (2H, m), 4.74-4.76 (1H, m), 5.29 (1H, d, J=10.4 Hz), 5.38 (1H, d, J=18.8 Hz), 5.94-6.03 (1H, m), 6.52-6.56 (1H, m), 6.79-6.81 (1H, m).

Workup

  1. customThe solvent was removed in vacuo
  2. customthe crude product was purified by flash column chromatography (Merck silica gel 60, 40-63 μm, 20% ethyl acetate in hexanes)

Sources & evidence

ORD record
ord-372d7bbe5cbe4924bb352dea83582b8a
Source dataset
uspto-grants-2009_09
Patent number
US07582754B2

Reaction notes

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