Hydrogen Bromide → 3-(Methyl(3-phenylpropyl)amino)-5-hydroxychroman

HRID 37655

反応式

HRID 37655 の反応式
[NH2:1][CH:2]1[CH2:11][C:10]2[C:5](=[CH:6][CH:7]=[CH:8][C:9]=2[O:12]C)[O:4][CH2:3]1.C([BH3-])#N.[Na+].[C:18]1([CH2:24][CH2:25][CH:26]=O)[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1.[CH2:28]=O.Br.[OH-].[Na+]>CO.C1(C)C=CC=CC=1.C(O)(=O)C>[CH3:28][N:1]([CH2:26][CH2:25][CH2:24][C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)[CH:2]1[CH2:11][C:10]2[C:5](=[CH:6][CH:7]=[CH:8][C:9]=2[OH:12])[O:4][CH2:3]1

参加物

10

反応物 6

HCID 260Hydrogen BromideHCID 712FormaldehydeHCID 7707BenzenepropanalHCID 14798Sodium HydroxideHCID 5003444Sodium cyanoborohydride2 回HCID 139289485-Methoxy-3,4-dihydro-2H-1-benzopyran-3-amine

生成物 1

HCID 190281563-(Methyl(3-phenylpropyl)amino)-5-hydroxychroman

試薬・触媒・溶媒 3

HCID 176Acetic Acid溶媒HCID 887Methanol溶媒HCID 1140Toluene溶媒

反応条件

温度
0 °C

実験手順

3-Amino-5-methoxychroman (Thorberg et al. Acta Pharm. Suec. 24(1987)) (2.0 g, 9.28 mmol) was dissolved in methanol (50 ml) and pH was adjusted to 6.0 with acetic acid. The solution was cooled to 0° C. and sodium cyanoborohydrid (0.87 g, 13.8 mmol) was added together with 3-phenylpropanal (1.22 ml, 9.28 mmol), the cooling was withdrawn and the solution was stirred at ambient temperature for 4 hours. Paraformaldehyde (0.42 g, 14 mmol) and sodium cyanoborohydride (0.87 g, 9.28 mmol) was added and stirring was continued overnight at ambient temperature. The solution was diluted with toluene and washed with water. Drying with sodium sulfate and evaporation to dryness gives an oil. The oil was purified by flash chromatography on silica gel by elution with ethylacete/hexane 1:4. The collected fractions were evaporated to give an oil. The oil was treated with HBr (47% aq.) at 120° C. for 1 hour. The solution was cooled and neutralised with sodium hydroxide and extracted with toluene. The organic phase was dried and evaporated to give the title compound as an oil. 13C-NMR: 22.502 29.09 33.47 38.19 53.66 67.75 102.04 109.20 110.46 125.78 127.05 128.36 142.20 155.29 158.28.

後処理

  1. customthe cooling was withdrawn
  2. stirringstirring
  3. waitwas continued overnight at ambient temperature
  4. washwashed with water
  5. dry with materialDrying with sodium sulfate and evaporation to dryness
  6. customgives an oil
  7. customThe oil was purified by flash chromatography on silica gel by elution with ethylacete/hexane 1:4
  8. customThe collected fractions were evaporated
  9. customto give an oil
  10. temperatureThe solution was cooled
  11. extractionextracted with toluene
  12. customThe organic phase was dried
  13. customevaporated

出典と根拠

ORDレコード
ord-256a891971184aa7b2d20ad7b29aba8d
出典データセット
uspto-grants-1995_05
特許番号
US05420151

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