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

HRID 1526154Notes

Reaction equation

HRID 1526154 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), [CAS 38762-41-3], 1,4-cyclohexanedione monoethyleneketal [CAS 4746-97-8], (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 DCM. The filtrate was washed with NaHCO3 (aqueous sat. solution), sodium chloride (aqueous sat. solution), dried (MgSO4) and concentrated in vacuo. The crude product thus obtained was purified by column chromatography (silica gel; DCM/AcOEt 4:1 as eluent). The desired fractions were collected and concentrated in vacuo to yield intermediate compound D38 (8.57 g, 85%).

Workup

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

Sources & evidence

ORD record
ord-c0a0dfe3f8f442939aee6c123b43f1b7
Source dataset
uspto-grants-2015_07
Patent number
US09085577B2

Reaction notes

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