3-Furancarboxaldehyde, tetrahydro- → HCID 59596849, compound

HRID 2264669Notes

Reaction equation

HRID 2264669 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][CH2:9][NH2:10])=[CH:4][C:3]=1[O:11][CH2:12][C:13]([F:16])([F:15])[F:14].[O:17]1[CH2:21][CH2:20][CH:19]([CH:22]=O)[CH2:18]1.[BH-](OC(C)=O)(OC(C)=O)OC(C)=O.[Na+].C([O-])(O)=O.[Na+]>ClCCl>[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][CH2:9][NH:10][CH2:22][CH:19]2[CH2:20][CH2:21][O:17][CH2:18]2)=[CH:4][C:3]=1[O:11][CH2:12][C:13]([F:15])([F:14])[F:16]

Participants

6

Reactant 4

HCID 1575683-Furancarboxaldehyde, tetrahydro-HCID 516892Sodium BicarbonateHCID 5049666Sodium triacetoxyborohydrideHCID 59596826HCID 59596826, compound

Product 1

HCID 59596849HCID 59596849, compoundYield 44.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of 500 mg (2.1 mmol) of 2-[4-fluoro-3-(2,2,2-trifluoro-ethoxy)-phenyl]-ethylamine, 210 mg (2.1 mmol) of tetrahydrofuran-3-carbaldehyde and 2 g of 4 Å molecular sieves in 30 ml of dry dichloromethane was stirred at room temperature for 30 minutes. 630 mg (2.9 mmol) of NaBH(OAc)3 were added portionwise. The reaction mixture was stirred for 4 hours at room temperature. An aqueous 5% solution of NaHCO3 was added and the product was extracted with dichloromethane. The crude product was purified by flash chromatography (dichloromethane/methanol/NH3 100:9:0.5 v:v:v). 300 mg (44% yield) of the title compound were isolated as an oil.

Workup

  1. stirringThe reaction mixture was stirred for 4 hours at room temperature
  2. extractionthe product was extracted with dichloromethane
  3. customThe crude product was purified by flash chromatography (dichloromethane/methanol/NH3 100:9:0.5 v:v:v)

Sources & evidence

ORD record
ord-4f6b14cd9a994d4b90b725f9c26bb9af
Source dataset
uspto-grants-2010_12
Patent number
US07855227B2

Reaction notes

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