Diisopropylethylamine → 5-(2,6-Dimethoxyphenyl)-1-(3-(2-methylthiazol-4-yl)benzyl)pyrrolidin-2-one

HRID 594387

반응식

HRID 594387 반응식
[NH2:1][CH:2]([C:9]1[C:14]([O:15][CH3:16])=[CH:13][CH:12]=[CH:11][C:10]=1[O:17][CH3:18])[CH2:3][CH2:4][C:5]([O:7]C)=O.CCN(C(C)C)C(C)C.[CH3:28][C:29]1[S:30][CH:31]=[C:32]([C:34]2[CH:35]=[C:36]([CH:39]=[CH:40][CH:41]=2)[CH:37]=O)[N:33]=1.[BH-](OC(C)=O)(OC(C)=O)OC(C)=O.[Na+].C([O-])(O)=O.[Na+]>ClCCCl.C(Cl)Cl>[CH3:18][O:17][C:10]1[CH:11]=[CH:12][CH:13]=[C:14]([O:15][CH3:16])[C:9]=1[CH:2]1[N:1]([CH2:37][C:36]2[CH:39]=[CH:40][CH:41]=[C:34]([C:32]3[N:33]=[C:29]([CH3:28])[S:30][CH:31]=3)[CH:35]=2)[C:5](=[O:7])[CH2:4][CH2:3]1

참가 물질

8

반응물 5

HCID 81531DiisopropylethylamineHCID 516892Sodium BicarbonateHCID 5049666Sodium triacetoxyborohydrideHCID 71277823-(2-Methyl-1,3-thiazol-4-yl)benzaldehydeHCID 69082397Methyl 4-amino-4-(2,6-dimethoxyphenyl)butanoate

생성물 1

HCID 690827085-(2,6-Dimethoxyphenyl)-1-(3-(2-methylthiazol-4-yl)benzyl)pyrrolidin-2-one

시약·촉매·용매 2

HCID 111,2-Dichloroethane용매HCID 6344Dichloromethane용매

실험 절차

A solution of the chlorhydrate salt of methyl 4-amino-4-(2,6-dimethoxyphenyl)butanoate (100 mg; 0.34 mmol; 1.0 equiv.) in anh. DCE (1.5 ml) was treated successively with DIPEA (0.12 ml; 0.69 mmol; 2.0 equiv.), 3-(2-methylthiazol-4-yl)benzaldehyde (70 mg; 0.34 mmol; 1.0 equiv.), and NaBH(OAc)3 (102 mg; 0.48 mmol; 1.4 equiv.). The resulting mixture was further stirred at rt, under nitrogen, for 72 h. DCM (50 ml) and a solution of aq. sat. NaHCO3 (35 ml) were then added. The organic layer was further washed with a solution of aq. sat. NaHCO3 (35 ml) and with brine (35 ml). The resulting organic layer was then dried over anh. MgSO4, filtered, and concentrated to dryness under reduced pressure. Purification by preparative HPLC afforded 5-(2,6-dimethoxyphenyl)-1-(3-(2-methylthiazol-4-yl)benzyl)pyrrolidin-2-one as a beige solid. LC-MS (conditions A): tR=0.81 min.; [M+H]+: 409.15 g/mol.

후처리

  1. washThe organic layer was further washed with a solution of aq. sat. NaHCO3 (35 ml) and with brine (35 ml)
  2. dry with materialThe resulting organic layer was then dried over anh. MgSO4
  3. filtrationfiltered
  4. concentrationconcentrated to dryness under reduced pressure
  5. customPurification by preparative HPLC

출처 및 근거

ORD 기록
ord-7dec92a7c99f4960b21cce724dc6f693
출처 데이터셋
uspto-grants-2016_01
특허 번호
US09242970B2

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