Triethylamine → 7-chloro-2-[(S)-2-([t-butyldimethylsilyloxy]methyl)pyrrolidine-1-carbonyl]thieno[3,2-b]pyridine

HRID 985191ノート

反応式

HRID 985191 の反応式
[Cl:1][C:2]1[CH:7]=[CH:6][N:5]=[C:4]2[CH:8]=[C:9]([C:11]([N:13]3[CH2:17][CH2:16][CH2:15][C@H:14]3[CH2:18][OH:19])=[O:12])[S:10][C:3]=12.[C:20]([Si:24]([CH3:27])([CH3:26])Cl)([CH3:23])([CH3:22])[CH3:21].C(N(CC)CC)C>O>[Cl:1][C:2]1[CH:7]=[CH:6][N:5]=[C:4]2[CH:8]=[C:9]([C:11]([N:13]3[CH2:17][CH2:16][CH2:15][C@H:14]3[CH2:18][O:19][Si:24]([C:20]([CH3:23])([CH3:22])[CH3:21])([CH3:27])[CH3:26])=[O:12])[S:10][C:3]=12

参加物

5

反応物 3

HCID 8471TriethylamineHCID 28928tert-Butyldimethylsilyl chlorideHCID 207677577-chloro-2-[(S)-2-(hydroxymethyl)pyrrolidine-1-carbonyl]thieno[3,2-b]pyridine

生成物 1

HCID 207677677-chloro-2-[(S)-2-([t-butyldimethylsilyloxy]methyl)pyrrolidine-1-carbonyl]thieno[3,2-b]pyridine収率 126.5%

試薬・触媒・溶媒 1

HCID 962Water溶媒

実験手順

To a stirred solution of 7-chloro-2-[(S)-2-(hydroxymethyl)pyrrolidine-1-carbonyl]thieno[3,2-b]pyridine 3a (4.50 g, 15 mmole) were added t-butyldimethylchlorosilane (3.18 g, 21 mmole) and triethylamine (3.4 ml, 2.47 g, 24 mmole). The resultant reaction mixture was stirred at ambient temperaure for 16 hours. The crude reaction mixture was poured into water (150 ml) and extracted with CH2Cl2 (150 ml). The combined organic extracts were washed with brine (150 ml), dried over Na2SO4 and concentrated, in vacuo, to give 7.8 g of an orange syrup, which was purified by silica gel chromatography. Elution with Et2O:hexane (67:33) and evaporation of the appropriate fractions gave 5.73 g (92%) of an off-white solid. 1H NMR (DMSO-d6): δ8.72 (1H, d, J=5.0 Hz), 8.07 (1H, s), 7.68 (1 H, d, J=5.0 Hz), 4.30-4.15 (1H, m), 3.94-3.67 (4H, m), 2.12-1.81 (4H, m), 0.85 (9H, s), 0.03 (3H, s), 0.00 (3H, s). Anal. Calcd. for C19H27N2O2SClSi: C, 55.52; H, 6.62; N, 6.82; S, 7.80; Cl, 8.63. Found: C, 55.49; H, 6.46; N, 6.92; S, 7.80; Cl, 8.88.

後処理

  1. customThe resultant reaction mixture
  2. customThe crude reaction mixture
  3. extractionextracted with CH2Cl2 (150 ml)
  4. washThe combined organic extracts were washed with brine (150 ml)
  5. dry with materialdried over Na2SO4
  6. concentrationconcentrated, in vacuo

出典と根拠

ORDレコード
ord-429e5074fe824167b4df19ac39e7872c
出典データセット
uspto-grants-2005_03
特許番号
US06869962B2

反応ノート

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