Hexane → 3-Methoxymethyl-3-(3-methoxy-phenyl)-1-methyl-azepan-2-one

HRID 1594853Notes

Reaction equation

HRID 1594853 reaction equation
[Li]CCCC.CCCCCC.CC1(C)CCCC(C)(C)N1.[CH3:22][O:23][C:24]1[CH:25]=[C:26]([CH:30]2[CH2:36][CH2:35][CH2:34][CH2:33][N:32]([CH3:37])[C:31]2=[O:38])[CH:27]=[CH:28][CH:29]=1.[CH3:39][O:40][CH2:41]I>C1COCC1>[CH3:39][O:40][CH2:41][C:30]1([C:26]2[CH:27]=[CH:28][CH:29]=[C:24]([O:23][CH3:22])[CH:25]=2)[CH2:36][CH2:35][CH2:34][CH2:33][N:32]([CH3:37])[C:31]1=[O:38]

Participants

7

Reactant 5

HCID 8058HexaneHCID 130352,2,6,6-TetramethylpiperidineHCID 139376Iodomethyl methyl etherHCID 2727906hexahydro-3-(3-methoxyphenyl)-1-methyl-2H-azepin-2-oneHCID 178418339Butyllithium

Product 1

HCID 217062403-Methoxymethyl-3-(3-methoxy-phenyl)-1-methyl-azepan-2-one

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To 1.6 M n-BuLi in hexane (3.38 mL, 5.42 mmol) at 0° C. was added a solution of 2,2,6,6-tetramethyl piperidine (0.91 mL, 5.42 mmol) in anh. THF (10 mL) over 5 min. A solution of 3-(3-methoxy-phenyl)-1-methyl-azepan-2-one (as described in Example 4, Step A) (0.632 g, 2.71 mmol) in anhydrous THF (10 mL) was added and stirred OC for 1 h. Iodomethyl methyl ether (0.275 mL, 3.25 mmol) was added. After stirring for 30 min, the reaction was quenched with H2O, concentrated in vacuo, diluted with EtOAc, washed with 5N HCl (100 mL), water and brine. The organic layer was dried (MgSO4) and concentrated to give the title compound.

Workup

  1. stirringAfter stirring for 30 min
  2. customthe reaction was quenched with H2O
  3. concentrationconcentrated in vacuo
  4. additiondiluted with EtOAc
  5. washwashed with 5N HCl (100 mL), water and brine
  6. dry with materialThe organic layer was dried (MgSO4)
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-ec2b0b360ba74e30beba54301bd0e5f9
Source dataset
uspto-grants-2001_09
Patent number
US06284755B1

Reaction notes

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