1,2-Dichloroethane → HCID 178420189, compound

HRID 2303330Notes

Reaction equation

HRID 2303330 reaction equation
[CH2:1]([CH:8]1[CH2:14][CH:13]2[NH:15][CH:10]([CH2:11][CH2:12]2)[CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[NH:16]1[CH:20]=[C:19]([CH2:21][CH2:22][CH:23]=[O:24])[N:18]=[CH:17]1.ClCCCl.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>C(Cl)(Cl)Cl.C([O-])([O-])=O.[Na+].[Na+]>[NH4+:15].[OH-:24].[CH2:1]([CH:8]1[CH2:14][CH:13]2[N:15]([CH2:23][CH2:22][CH2:21][C:19]3[N:18]=[CH:17][NH:16][CH:20]=3)[CH:10]([CH2:11][CH2:12]2)[CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

8

Reactant 4

HCID 111,2-DichloroethaneHCID 5049666Sodium triacetoxyborohydrideHCID 18461105338733-58-7HCID 178520508HCID 178520508, compound

Product 2

HCID 14923Ammonium HydroxideHCID 178420189HCID 178420189, compoundYield 130.1%

Reagents, catalysts & solvents 2

HCID 6212ChloroformSolventHCID 10340Sodium CarbonateSolvent

Procedure

A mixture of 0.25 g of 3-benzyl-8-aza-bicyclo[3.2.1]octane, 0.45 g of 3-(1H-imidazol-4-yl)-propionaldehyde, 5 mL of 1,2-dichloroethane and 0.5 g of sodium triacetoxyborohydride was stirred at room temperature for 48 h. The reaction mixture was diluted with 50 mL chloroform and 10 mL saturated aqueous Na2CO3 and the layers separated. The aqueous layer was extracted with 2×25 mL of chloroform and the combined organic layers dried over magnesium sulfate and concentrated under reduced pressure. Purification by chromatography eluting with 90:10:1 CHCl3:MeOH:NH4OH gave 0.25 g of 3-benzyl-8-[3-(1H-imidazol-4-yl)-propyl]-8-aza-bicyclo[3.2.1]octane as a 2:1 mixture of exo:endo isomers. MS (m+1)=310.3; 1H NMR (400 MHz, CDCl3) 7.5-7.1 (complex, 6H), 6.75 (s, 1H), 3.22 (s, 2H), 2.75 (m, 2.6 H), 2.5 (d, 0.7×2H), 2.45 (m, 2H), 2.1 (m, 2H), 1.95 (m, 2H), 1.8 (m, 3H), 1.5 (m, 4H).

Workup

  1. customthe layers separated
  2. extractionThe aqueous layer was extracted with 2×25 mL of chloroform
  3. dry with materialthe combined organic layers dried over magnesium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customPurification by chromatography
  6. washeluting with 90:10:1 CHCl3

Sources & evidence

ORD record
ord-803556e40d5647d1820ec53668b0388a
Source dataset
uspto-grants-2002_08
Patent number
US06432976B1

Reaction notes

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