Benzaldehyde → {4-[4-(2-Benzylaminoethoxy)phenyl]butyl}carbamic acid benzyl ester

HRID 1696830ノート

反応式

HRID 1696830 の反応式
[CH:1]1[CH:6]=[CH:5][C:4]([CH:7]=O)=[CH:3][CH:2]=1.[CH2:9]([O:16][C:17](=[O:33])[NH:18][CH2:19][CH2:20][CH2:21][CH2:22][C:23]1[CH:28]=[CH:27][C:26]([O:29][CH2:30][CH2:31][NH2:32])=[CH:25][CH:24]=1)[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>ClC(Cl)C>[CH2:9]([O:16][C:17](=[O:33])[NH:18][CH2:19][CH2:20][CH2:21][CH2:22][C:23]1[CH:28]=[CH:27][C:26]([O:29][CH2:30][CH2:31][NH:32][CH2:7][C:4]2[CH:5]=[CH:6][CH:1]=[CH:2][CH:3]=2)=[CH:25][CH:24]=1)[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1

参加物

5

反応物 3

HCID 240BenzaldehydeHCID 5049666Sodium triacetoxyborohydrideHCID 59750599Benzyl (4-(4-(2-aminoethoxy)phenyl)butyl)carbamate

生成物 1

HCID 58100148{4-[4-(2-Benzylaminoethoxy)phenyl]butyl}carbamic acid benzyl ester収率 43%

試薬・触媒・溶媒 1

HCID 63651,1-Dichloroethane溶媒

実験手順

Benzyaldehyde (0.74 ml, 7.31 mmol) was added to a solution of 4-[4-(2-aminoethoxy)phenyl]butylcarbamic acid benzyl ester (15) (5.00 g (˜50% purity by NMR), 7.30 mmol) dissolved in anhydrous dichloroethane (50 mL). The resulting solution was stirred at ambient temperature for 7 h. Sodium triacetoxyborohydride (4.10 g, 19.35 mmol) was added slowly and the reduction continued for 60 h. The reaction was quenched with aqueous sodium bicarbonate (50 mL) and then extracted with ethyl acetate (3×25 mL). The combined organic extracts were washed sequentially with water and brine, and dried over anhydrous sodium sulfate. A white solid precipitated out during the drying and collected by dissolving it in dichloromethane and then filtering off the solid sodium sulfate. The filtrate was concentrated and dried under vacuum to give 16 (1.35 g, 43%) as a white solid: 1H NMR (500 MHz, CDCl3) δ 1.45-1.62 (m, 4H), 2.54 (t, 2H), 3.07-3.22 (m, 4H), 3.88 (s, 2H), 4.10 (t, 2H), 4.73 (br, 1H), 5.09 (s, 2H), 6.79 (d, 2H), 7.04 (d, 2H), 7.28-7.39 (m, 10H); m/z (ESI) 433 [C27H32N2O3+H]+.

後処理

  1. waitthe reduction continued for 60 h
  2. customThe reaction was quenched with aqueous sodium bicarbonate (50 mL)
  3. extractionextracted with ethyl acetate (3×25 mL)
  4. washThe combined organic extracts were washed sequentially with water and brine
  5. dry with materialdried over anhydrous sodium sulfate
  6. customA white solid precipitated out during the drying and
  7. customcollected
  8. dissolutionby dissolving it in dichloromethane
  9. filtrationfiltering off the solid sodium sulfate
  10. concentrationThe filtrate was concentrated
  11. customdried under vacuum

出典と根拠

ORDレコード
ord-a30260aceb864b0a9df4a8d672121c50
出典データセット
uspto-grants-2012_04
特許番号
US08163758B2

反応ノート

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