4-Fluoro-2-(trifluoromethyl)benzaldehyde → HCID 86608733, compound

HRID 1436929Notes

Reaction equation

HRID 1436929 reaction equation
[NH2:1][C@H:2]1[CH2:7][CH2:6]C[N:4]([C:8]([O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[O:9])[CH2:3]1.[F:15][C:16]1[CH:23]=[CH:22][C:19]([CH:20]=O)=[C:18]([C:24]([F:27])([F:26])[F:25])[CH:17]=1.[BH4-].[Na+]>CO>[F:15][C:16]1[CH:23]=[CH:22][C:19]([CH2:20][NH:1][C@H:2]2[CH2:7][CH2:6][N:4]([C:8]([O:10][C:11]([CH3:12])([CH3:13])[CH3:14])=[O:9])[CH2:3]2)=[C:18]([C:24]([F:25])([F:26])[F:27])[CH:17]=1

Participants

5

Reactant 3

HCID 5229404-Fluoro-2-(trifluoromethyl)benzaldehydeHCID 1501975tert-butyl (3S)-3-aminopiperidine-1-carboxylateHCID 4311764Sodium borohydride

Product 1

HCID 86608733HCID 86608733, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

1,1-Dimethylethyl (3S)-3-aminopiperidine-1-carboxylate (5 g) and 4-fluoro-2-(trifluoromethyl)benzaldehyde (5.15 g, 26.8 mmol) were allowed to stir in methanol for 16 h at room temperature. Sodium borohydride (1.62 g, 26.8 mmol) was then added portionwise. The resulting solution was further stirred for 2 h at room temperature. The solvent was evaporated in vacuo, water was added, and the solution extracted with dichloromethane. The organic extracts were absorbed onto a methanol washed cationic ion exchange resin (Isolute™ SCX-2). The basic components were recovered from the column by elution with 7N ammonia in methanol. The resultant solution was concentrated in vacuo to yield the desired compound as an oil. This was further purified by column chromatography on silica gel, eluting with ethyl acetate/iso-hexane (0:100 to 40:60). The title compound was used in subsequent reactions without further purification. 1H NMR (300 MHz, CDCl3) δH: 7.37-7.28 (m, 2H), 7.24-7.20 (m, 1H), 3.80 (s, 2H), 3.52-3.48 (m, 2H), 3.32 (m, 3H), 3.12 (m, 1H), 2.08-2.0 (m, 1H), 1.75 (m, 1H), 1.45 (s, 9H).

Workup

  1. customThe solvent was evaporated in vacuo, water
  2. additionwas added
  3. extractionthe solution extracted with dichloromethane
  4. customThe organic extracts were absorbed onto a methanol washed cationic ion exchange resin (Isolute™ SCX-2)
  5. customThe basic components were recovered from the column by elution with 7N ammonia in methanol
  6. concentrationThe resultant solution was concentrated in vacuo

Sources & evidence

ORD record
ord-e2e3bef0b4a345f18e1d7b97d5bc3bba
Source dataset
uspto-grants-2009_11
Patent number
US07619096B2

Reaction notes

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