2-Benzofurancarboxaldehyde → HCID 68575168, compound

HRID 2111922Notes

Reaction equation

HRID 2111922 reaction equation
C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].[C:15]([O:19][C:20]([N:22]1[CH2:27][CH2:26][CH:25]([NH:28][CH2:29][CH2:30][CH:31]([CH3:33])[CH3:32])[CH2:24][CH2:23]1)=[O:21])([CH3:18])([CH3:17])[CH3:16].[O:34]1[C:38]2[CH:39]=[CH:40][CH:41]=[CH:42][C:37]=2[CH:36]=[C:35]1[CH:43]=O.C([O-])(O)=O.[Na+]>ClCCl>[C:15]([O:19][C:20]([N:22]1[CH2:23][CH2:24][CH:25]([N:28]([CH2:43][C:35]2[O:34][C:38]3[CH:39]=[CH:40][CH:41]=[CH:42][C:37]=3[CH:36]=2)[CH2:29][CH2:30][CH:31]([CH3:33])[CH3:32])[CH2:26][CH2:27]1)=[O:21])([CH3:18])([CH3:17])[CH3:16]

Participants

6

Reactant 4

HCID 613412-BenzofurancarboxaldehydeHCID 516892Sodium BicarbonateHCID 5049666Sodium triacetoxyborohydrideHCID 43652145HCID 43652145, compound

Product 1

HCID 68575168HCID 68575168, compoundYield 105.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Sodium triacetoxyborohydride (0.88 g, 4.16 mmol) is added to a stirred solution of 4-(3-methyl-butylamino)-piperidine-1-carboxylic acid tert-butyl ester (0.75 g, 2.77 mmol), benzofuran-2-carboxaldehyde (0.50 g, 3.46 mmol), and dichloromethane (14 ml). The reaction is stirred overnight at room temperature under nitrogen. The reaction is poured into aqueous saturated NaHCO3 (50 ml) and extracted with dichloromethane (25 ml×3). The organic layer is washed with aqueous saturated NaHCO3 and dried over Na2SO4, and filtered. The crude product is concentrated on a rotary evaporator and purified by flash chromatography on silica gel eluting with 0-30% (1:2 (10% NH4OH in methanol):ethanol) to yield (1.17 g) of 4-{[(benzofuran-2-yl)methyl]-(3-methylbutyl)-amino}-piperidine-1-carboxylic acid tert-butyl ester: mass spectrum (ion spray): m/z=401 (M+1); 1H NMR (CDCl3): δ=7.57-7.41 (2H, m), 7.30-7.16 (2H, m), 6.55 (1H, s), 4.15 (2H, brs), 3.81 (2H, s), 2.75-2.56 (6H, m), 1.80 (2H, brd), 1.63-1.53 (3H, m), 1.46 (9H, s), 1.42-1.33 (1H, m), 0.92-0.85 (6H, m).

Workup

  1. extractionextracted with dichloromethane (25 ml×3)
  2. washThe organic layer is washed with aqueous saturated NaHCO3
  3. dry with materialdried over Na2SO4
  4. filtrationfiltered
  5. concentrationThe crude product is concentrated on a rotary evaporator
  6. custompurified by flash chromatography on silica gel eluting with 0-30% (1:2 (10% NH4OH in methanol):ethanol)

Sources & evidence

ORD record
ord-6e0c4636e2544f7c9137b0c59baf6d62
Source dataset
uspto-grants-2009_04
Patent number
US07521462B2

Reaction notes

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