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

HRID 399645

반응식

HRID 399645 반응식
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

참가 물질

5

반응물 3

HCID 15312-Amino-2-methyl-1,3-propanediolHCID 8471TriethylamineHCID 109361336-Bromomethylchrysene2회

생성물 1

HCID 57062Crisnatol수율 71%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-e937f227fb454251a5f112af9faad32b
출처 데이터셋
uspto-grants-1998_10
특허 번호
US05821387

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