Acetic Acid → HCID 22620115, compound

HRID 840617Notes

Reaction equation

HRID 840617 reaction equation
C(O[C:4](=[O:20])[CH2:5][CH:6]1[CH2:11][CH:10]([CH2:12][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[CH2:9][CH2:8][C:7]1=O)C.C(O)(=O)C.[CH2:25]([NH2:32])[C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>C(Cl)(Cl)Cl.C([O-])([O-])=O.[Na+].[Na+].ClCCCl>[CH2:25]([N:32]1[CH:7]2[CH:6]([CH2:11][CH:10]([CH2:12][C:13]3[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=3)[CH2:9][CH2:8]2)[CH2:5][C:4]1=[O:20])[C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1

Participants

8

Reactant 4

HCID 176Acetic AcidHCID 7504BenzylamineHCID 5049666Sodium triacetoxyborohydrideHCID 69940430HCID 69940430, compound

Product 1

HCID 22620115HCID 22620115, compoundYield 53.7%

Reagents, catalysts & solvents 3

HCID 111,2-DichloroethaneSolventHCID 6212ChloroformSolventHCID 10340Sodium CarbonateSolvent

Procedure

A mixture of 8 g of (5-benzyl-2-oxo-cyclohexyl)-acetic acid ethyl ester, 3.4 g of acetic acid, 3.75 g of benzylamine, 50 mL of 1,2-dichloroethane and 7.7 g of sodium triacetoxyborohydride was stirred at room temperature for 48 h. The reaction mixture was diluted with 100 mL chloroform and 40 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 50% ethyl acetate in hexane gave 5 g of 1,5-dibenzyl-octahydro-indol-2-one.

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 50% ethyl acetate in hexane

Sources & evidence

ORD record
ord-7ce01fd0f88b48f2b1c404653fc994df
Source dataset
uspto-grants-2002_04
Patent number
US06369076B1

Reaction notes

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