Sodium triacetoxyborohydride → HCID 178509524、化合物

HRID 1066904ノート

反応式

HRID 1066904 の反応式
[F:1][C:2]1[CH:3]=[C:4]([CH:10]=[CH:11][CH:12]=1)[O:5][CH:6]1[CH2:9][NH:8][CH2:7]1.O=[C:14]1[CH2:19][CH2:18][CH:17]([C:20]2[C:28]3[C:23](=[CH:24][CH:25]=[C:26]([C:29]#[N:30])[CH:27]=3)[NH:22][CH:21]=2)[CH2:16][CH2:15]1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>C(Cl)Cl>[F:1][C:2]1[CH:3]=[C:4]([CH:10]=[CH:11][CH:12]=1)[O:5][CH:6]1[CH2:9][N:8]([C@@H:14]2[CH2:15][CH2:16][C@H:17]([C:20]3[C:28]4[C:23](=[CH:24][CH:25]=[C:26]([C:29]#[N:30])[CH:27]=4)[NH:22][CH:21]=3)[CH2:18][CH2:19]2)[CH2:7]1

参加物

5

反応物 3

HCID 5049666Sodium triacetoxyborohydrideHCID 112418863-(4-oxocyclohexyl)-1H-indole-5-carbonitrileHCID 155219743-(3-Fluorophenoxy)azetidine

生成物 1

HCID 178509524HCID 178509524、化合物収率 32.3%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

To a solution of 0.170 g of 3-(3-fluoro-phenoxy)-azetidine in 10 mL of CH2Cl2 was added 0.180 g of 3-(4-oxo-cyclohexyl)-1H-indole-5-carbonitrile followed by 0.420 g of sodium triacetoxyborohydride. The reaction was stirred at room temperature overnight. It was quenched with 1N NaOH and the product was extracted with ether. The organic phase was washed with water, dried over magnesium sulfate, filtered, and concentrated. The product was filtered through 150 mL of silica gel using 50% ethyl acetate/hexane, 75% ethyl acetate/hexane and finally 100% ethyl acetate to give 0.095 g of the desired product: mp 187-190° C. 1H NMR (300 MHz, CDCl3) δ 1.51-1.65 (m, 2H), 1.69-1.75 (m, 4H), 1.77-1.90 (m, 2H), 2.45 (m, 1H), 2.90 (m, 1H), 3.03 (dd, 2H), 3.81 (dd, 2H), 4.77 (m, 1H), 6.53-6.59 (m, 2H), 6.66 (m, 1H), 7.13-7.22 (m, 2H), 7.39 (dd, 2H), 8.00 (s, 1H), 8.28 (s, 1H); MS (ES) m/z (relative intensity): 390 (M++H).

後処理

  1. customIt was quenched with 1N NaOH
  2. extractionthe product was extracted with ether
  3. washThe organic phase was washed with water
  4. dry with materialdried over magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated
  7. filtrationThe product was filtered through 150 mL of silica gel using 50% ethyl acetate/hexane, 75% ethyl acetate/hexane and finally 100% ethyl acetate

出典と根拠

ORDレコード
ord-214c98769c9a47378ef1b4ddd00d9290
出典データセット
uspto-grants-2001_06
特許番号
US06245799B1

反応ノート

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