tert-Butyl piperazine-1-carboxylate → HCID 67513971, 화합물

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[F:1][CH:2]([F:15])[O:3][C:4]1[CH:11]=[C:10]([CH2:12][CH:13]=O)[CH:9]=[CH:8][C:5]=1[C:6]#[N:7].[C:16]([N:23]1[CH2:28][CH2:27][NH:26][CH2:25][CH2:24]1)([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17].[BH-](OC(C)=O)(OC(C)=O)OC(C)=O.[Na+]>C(Cl)Cl>[C:19]([O:18][C:16]([N:23]1[CH2:28][CH2:27][N:26]([CH2:13][CH2:12][C:10]2[CH:9]=[CH:8][C:5]([C:6]#[N:7])=[C:4]([O:3][CH:2]([F:15])[F:1])[CH:11]=2)[CH2:25][CH2:24]1)=[O:17])([CH3:22])([CH3:20])[CH3:21]

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실험 절차

A solution of crude compound 2-(difluoromethoxy)-4-(2-oxoethyl)benzonitrile (100 mg, 0.48 mmol), N-Boc Piperazine (100 mg, 0.54 mmol) and NaBH(OAc)3 (0.4 g, 2 mmol) in 20 mL of anhydrous DCM was stirred at ambient temperature overnight. The reaction mixture was added 50 mL of DCM, washed with brine. The organic layer was dried over anhydrous sodium sulfate and concentrated. The residue was purified with prep-TLC to afford tert-butyl-4-{2-[4-cyano-3-(difluoromethoxy)phenyl]ethyl}piperazine-1-carboxylate (50 mg, 27% yield). The material was further treated with TFA to remove the Boc group. The crude product was used directly in the next step. MS: m/e 282 (M+1)+.