Acetic Acid → N-{[(7S)-3,4-Dimethoxybicyclo[4.2.0]octa-1,3,5-trien-7-yl]-methyl}cyclopentanamine

HRID 657544Notes

Reaction equation

HRID 657544 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:8](=[CH:9][C:10]=1[O:11][CH3:12])[C@@H:7]([CH2:13][NH2:14])[CH2:6]2.[C:15]1(=O)[CH2:19][CH2:18][CH2:17][CH2:16]1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].C(O)(=O)C.[OH-].[Na+]>ClCCl>[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:8](=[CH:9][C:10]=1[O:11][CH3:12])[C@@H:7]([CH2:13][NH:14][CH:15]1[CH2:19][CH2:18][CH2:17][CH2:16]1)[CH2:6]2

Participants

7

Reactant 5

HCID 176Acetic AcidHCID 8452CyclopentanoneHCID 14798Sodium HydroxideHCID 5049666Sodium triacetoxyborohydrideHCID 115066164,5-Dimethoxy-1-(aminomethyl)benzocyclobutane, (S)-

Product 1

HCID 68533347N-{[(7S)-3,4-Dimethoxybicyclo[4.2.0]octa-1,3,5-trien-7-yl]-methyl}cyclopentanamine

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

At ambient temperature, 2.9 g (15 mmol) of {[(7S)-3,4-dimethoxybicyclo[4.2.0]octa-1,3,5-trien-7-yl]methyl}amine and 1.3 mL (15 mmol/1 eq.) of cyclopentanone are mixed into 60 mL of dichloromethane. There are then added 4.8 g (22.5 mmol/1.5 eq.) of sodium triacetoxyborohydride and then 0.86 mL (15 mmol/1 eq.) of acetic acid, and stirring is carried out at ambient temperature for 4 hours. 90 mL of 1N sodium hydroxide solution are then poured in; extraction with two 120 mL quantities of ether is then carried out. The combined organic phases are washed with 90 mL of water and then with 90 mL of saturated aqueous sodium chloride solution and are then dried over magnesium sulphate. After filtration and concentration, the desired product is collected.

Workup

  1. extractionextraction with two 120 mL quantities of ether
  2. washThe combined organic phases are washed with 90 mL of water
  3. dry with materialwith 90 mL of saturated aqueous sodium chloride solution and are then dried over magnesium sulphate
  4. filtrationAfter filtration and concentration
  5. customthe desired product is collected

Sources & evidence

ORD record
ord-624ab72b77a8465ebef18865ef97da56
Source dataset
uspto-grants-2011_12
Patent number
US08076325B2

Reaction notes

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