2-Amino-2-methyl-1,3-propanediol → Crisnatol

HRID 399645

反応式

HRID 399645 の反応式
Br[CH2:2][C:3]1[CH:4]=[C:5]2[C:14](=[C:15]3[C:20]=1[CH:19]=[CH:18][CH:17]=[CH:16]3)[CH:13]=[CH:12][C:11]1[CH:10]=[CH:9][CH:8]=[CH:7][C:6]2=1.[NH2:21][C:22]([CH3:27])([CH2:25][OH:26])[CH2:23][OH:24].C(N(CC)CC)C>O1CCCC1>[CH:10]1[C:11]2[CH:12]=[CH:13][C:14]3[C:5](=[CH:4][C:3]([CH2:2][NH:21][C:22]([CH3:27])([CH2:25][OH:26])[CH2:23][OH:24])=[C:20]4[C:15]=3[CH:16]=[CH:17][CH:18]=[CH:19]4)[C:6]=2[CH:7]=[CH:8][CH:9]=1

参加物

5

反応物 3

HCID 15312-Amino-2-methyl-1,3-propanediolHCID 8471TriethylamineHCID 109361336-Bromomethylchrysene2 回

生成物 1

HCID 57062Crisnatol収率 71%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

A mixture of 6-bromomethylchrysene (4.82 g, 15 mmol), 2-amino-2-methylpropane-1,3diol (3.15 g, 30 mmol), and triethylamine (1.67 g, 16.5 mmol) was refluxed in tetrahydrofuran (75 mL) under nitrogen. After one hour all the solids had dissolved and NMR analysis indicated that the 6-bromomethylchrysene had been consumed. Water (150 mL) was added and the mixture was cooled to ambient temperature. The solids were collected by filtration, washed with water (3×30 mL), and dried in vacuo to give 3.67 g (71% yield) of 2-(6-chrysenylmethylamino)-2-methylpropane-1,3diol. 1H NMR (CDCl3) 1.19 (s, 3 H), 1.81 (br s, 1 H), 3.53 (d, J=5.0 Hz, 2 H), 4.39 (s, 2 H), 4.58 (t, J=5.0 Hz, 2 H), 7.78 (m, 4 H), 8.11 (m, 2 H), 8.45 (d, J=8.4 Hz, 1 H), 8.9 (m, 4 H).

後処理

  1. dissolutionAfter one hour all the solids had dissolved
  2. customhad been consumed
  3. additionWater (150 mL) was added
  4. filtrationThe solids were collected by filtration
  5. washwashed with water (3×30 mL)
  6. customdried in vacuo

出典と根拠

ORDレコード
ord-e937f227fb454251a5f112af9faad32b
出典データセット
uspto-grants-1998_10
特許番号
US05821387

関連ノート

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