1,4-Dioxaspiro[4.5]decan-8-one → HCID 43168144, compound

HRID 1627024Notes

Reaction equation

HRID 1627024 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([NH2:8])=[C:4]([Cl:9])[CH:3]=1.[CH2:10]1[O:20][C:13]2([CH2:18][CH2:17][C:16](=O)[CH2:15][CH2:14]2)[O:12][CH2:11]1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>ClCCCl.C(O)(=O)C>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][CH:16]2[CH2:17][CH2:18][C:13]3([O:20][CH2:10][CH2:11][O:12]3)[CH2:14][CH2:15]2)=[C:4]([Cl:9])[CH:3]=1

Participants

6

Reactant 3

HCID 5674151,4-Dioxaspiro[4.5]decan-8-oneHCID 6101694-Bromo-2-chloroanilineHCID 5049666Sodium triacetoxyborohydride

Product 1

HCID 43168144HCID 43168144, compound

Reagents, catalysts & solvents 2

HCID 111,2-DichloroethaneSolventHCID 176Acetic AcidSolvent

Procedure

A mixture of 4-bromo-2-chloro-phenylamine (6 g, 29.06 mmol), 1,4-cyclohexanedione monoethyleneketal (6.908 g, 43.59 mmol), and sodium triacetoxy-borohydride (9.239 g, 43.59 mmol) in DCE (100 ml) and acetic acid (0.2 ml) was stirred at r.t. for 2 days. The mixture was then filtered through a pad of diatomaceous earth and washed with dichloromethane. The filtrate was washed with NaHCO3 (aqueous sat. solution), sodium chloride (aqueous sat. solution), dried (MgSO4) and evaporated in vacuo. The crude product thus obtained was purified by column chromatography (silica gel; DCM/EtOAc 4:1 as eluent). The desired fractions were collected and evaporated in vacuo to yield intermediate compound D33 (8.57 g, 85%).

Workup

  1. filtrationThe mixture was then filtered through a pad of diatomaceous earth
  2. washwashed with dichloromethane
  3. washThe filtrate was washed with NaHCO3 (aqueous sat. solution), sodium chloride (aqueous sat. solution)
  4. dry with materialdried (MgSO4)
  5. customevaporated in vacuo

Sources & evidence

ORD record
ord-3fb15651e41d41c5a842b1cbd08de6d1
Source dataset
uspto-grants-2014_07
Patent number
US08785486B2

Reaction notes

Loading…