Hexane → Hexahydro-3-(3-methoxyphenyl)-2H-azepin-2-one
Reaction equation
[Li]CCCC.CCCCCC.CC1(C)CCCC(C)(C)N1.C[Si](C)(C)[N:24]1[CH2:30][CH2:29][CH2:28][CH2:27][CH2:26][C:25]1=[O:31].Cl[C:35]1[CH:40]=[CH:39][CH:38]=[CH:37][C:36]=1[O:41][CH3:42]>C1COCC1>[CH3:42][O:41][C:36]1[CH:35]=[C:40]([CH:26]2[CH2:27][CH2:28][CH2:29][CH2:30][NH:24][C:25]2=[O:31])[CH:39]=[CH:38][CH:37]=1Participants
Procedure
To 1.6 M n-BuLi in hexane (31.3 mL, 50 mmol) at 0° C. was added a solution of 2,2,6,6-tetramethyl piperidine (8.43 mL, 50 mmol) in anhydrous THF (100 mL) over 5 min. 1-Trimethylsilanyl-azepan-2-one (as described in Step F above) (9.26 g, 50 mmol) in anhydrous THF (20 mL) was added. After stirring the reaction mixture for 10 min a further portion of 1.6M n-BuLi in hexane (31.3 mL, 50 mmol) was added, the mixture stirred for 10 min, and 2-chloroanisole (6.34 mL, 50 mmol) was added. After stirring for 30 min under Ar, the reaction was quenched with H2O, stirred for 30 min, concentrated in vacuo, diluted with EtOAc, washed with 5N HCl (100 mL) and brine. The organic layer was dried (MgSO4), concentrated and purified using SiO2 chromatography (0.5% MeOH/CH2Cl2) to give the title compound.
Workup
- additionwas added
- stirringAfter stirring for 30 min under Ar
- customthe reaction was quenched with H2O
- stirringstirred for 30 min
- concentrationconcentrated in vacuo
- additiondiluted with EtOAc
- washwashed with 5N HCl (100 mL) and brine
- dry with materialThe organic layer was dried (MgSO4)
- concentrationconcentrated
- custompurified
Sources & evidence
- ORD record
- ord-185c4bcc30e04605b6de41bbcb7cc409
- Source dataset
- uspto-grants-2001_11
- Patent number
- US06316436B1
Reaction notes
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