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

HRID 594387ノート

反応式

HRID 594387 の反応式
[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

参加物

8

反応物 5

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 111,2-Dichloroethane溶媒HCID 6344Dichloromethane溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-7dec92a7c99f4960b21cce724dc6f693
出典データセット
uspto-grants-2016_01
特許番号
US09242970B2

反応ノート

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