Benzylamine → (2s,3r)-Isopropyl 3-(allyloxy)-4-(benzylamino)-2-((6-(2,5-dimethyl-1h-pyrrol-1-yl)-4-methylpyridin-2-yl)methyl)butanoate

HRID 1942945

反応式

HRID 1942945 の反応式
[CH2:1]([O:4][C@@H:5]([CH:28]=O)[C@H:6]([CH2:13][C:14]1[CH:19]=[C:18]([CH3:20])[CH:17]=[C:16]([N:21]2[C:25]([CH3:26])=[CH:24][CH:23]=[C:22]2[CH3:27])[N:15]=1)[C:7]([O:9][CH:10]([CH3:12])[CH3:11])=[O:8])[CH:2]=[CH2:3].[CH2:30]([NH2:37])[C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1>C1COCC1>[CH2:1]([O:4][C@@H:5]([CH2:28][NH:37][CH2:30][C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1)[C@H:6]([CH2:13][C:14]1[CH:19]=[C:18]([CH3:20])[CH:17]=[C:16]([N:21]2[C:25]([CH3:26])=[CH:24][CH:23]=[C:22]2[CH3:27])[N:15]=1)[C:7]([O:9][CH:10]([CH3:11])[CH3:12])=[O:8])[CH:2]=[CH2:3]

参加物

4

反応物 2

HCID 7504BenzylamineHCID 44543305(2S,3R)-Isopropyl 3-(allyloxy)-2-((6-(2,5-dimethyl-1H-pyrrol-1-yl)-4-methylpyridin-2-yl)methyl)-4-oxobutanoate

生成物 1

HCID 59582524(2s,3r)-Isopropyl 3-(allyloxy)-4-(benzylamino)-2-((6-(2,5-dimethyl-1h-pyrrol-1-yl)-4-methylpyridin-2-yl)methyl)butanoate収率 92%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

To a solution of 16 (240 mg, 0.6 mmol) in THF (5 mL) was added benzylamine (100 μL, 0.9 mmol) followed by NaHB(OAc)3 (153 mg, 0.72 mmol). The reaction was allowed to stir for an additional 3 h then partitioned between EtOAc (100 mL) and brine (50 mL). The aqueous layer was extracted with EtOAc (50 mL). The combined organic layers were dried over Na2SO4 and concentrated. The crude product was purified by flash column chromatography (EtOAc:hexanes, 1:2-1:1) to give 19 (270 mg, 0.55 mmol, 92%) as a colorless oil: 1H NMR (500 MHz, CDCl3) δ 0.99-1.01 (d, J=6.5 Hz, 3H), 1.09-1.11 (d, J=6.5 Hz, 3H), 2.13 (s, 6H), 2.37 (s, 3H), 2.76-2.85 (ddd, J=4.5, 5.0, 12.5, Hz, 1H), 2.98-3.08 (ddd, J=5.5, 14.0, 15.5, Hz, 1H), 3.49-3.52 (m, 1H), 3.81 (s, 2H), 3.82-3.89 (m, 1H), 4.04-4.08 (dd, J=6.0, 12.5, Hz, 1H), 4.09-4.12 ((dd, J=5.5, 13.0, Hz, 1H), 4.86-4.89 (m, 1H), 5.13-5.15 (dd, J=1.0, 10.0, Hz, 1H), 5.23-5.28 (dd, J=1.5, 17.0, Hz, 1H), 5.86-5.91 (m, 3H), 6.85 (s, 1H), 7.00 (s, 1H), 7.20-7.27 (m, 2H), 7.27-7.35 (m, 3H); 13C NMR (125 MHz, CDCl3) δ 13.6, 21.2, 21.8, 21.9, 35.1, 47.6, 49.9, 54.0, 68.0, 71.4, 79.4, 106.8, 117.2, 120.3, 123.4, 127.2, 128.4, 128.6, 128.8, 134.9, 140.4, 149.5, 151.7, 159.4, 173.0; LCQ-MS (M+H+) calcd for C30H40N3O3 490. found 490; LC-TOF-MS (M+H+) calcd for C30H40N3O3 490.30697. found 490.30644.

後処理

  1. customthen partitioned between EtOAc (100 mL) and brine (50 mL)
  2. extractionThe aqueous layer was extracted with EtOAc (50 mL)
  3. dry with materialThe combined organic layers were dried over Na2SO4
  4. concentrationconcentrated
  5. customThe crude product was purified by flash column chromatography (EtOAc:hexanes, 1:2-1:1)

出典と根拠

ORDレコード
ord-f4c6423c31654b4d85cd361928d98803
出典データセット
uspto-grants-2013_03
特許番号
US08389731B2

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