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Formaldehyde → HCID 14146237, 화합물

HRID 1253287
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HRID 1253287 반응식
[CH3:1][O:2][C:3](=[O:23])[CH2:4][C:5]1([CH2:21][CH3:22])[C:10]2[NH:11][C:12]3[C:17]([C:9]=2[CH:8](N)[CH2:7][O:6]1)=[CH:16][CH:15]=[CH:14][C:13]=3[CH2:18][CH3:19].[OH2:24].C=O>C1COCC1>[CH3:1][O:2][C:3](=[O:23])[CH2:4][C:5]1([CH2:21][CH3:22])[C:10]2[NH:11][C:12]3[C:17]([C:9]=2[CH:8]([OH:24])[CH2:7][O:6]1)=[CH:16][CH:15]=[CH:14][C:13]=3[CH2:18][CH3:19]
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

5

반응물 3

HCID 712FormaldehydeHCID 962WaterHCID 4196618Methyl 4-amino-1,8-diethyl-1,3,4,9-tetrahydropyrano[3,4-b]indole-1-acetate

생성물 1

HCID 14146237HCID 14146237, 화합물수율 80.5%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

To a solution of 4-amino-1,8-diethyl-1,3,4,9-tetrahydropyrano[3,4-b]indole-1-acetic acid methyl ester (prepared in Example 1) (1.5 g, 0.0047 mol) in THF (5 mL) was added water (5 mL) and paraformaldehyde (0.5 g). The mixture was heated at reflux for 1 hour, then concentrated in vacuo and the residue extracted with ether. The ether extracts were washed with saturated NaHCO3 solution, brine, and dried and concentrated in vacuo. Elution from a silica gel column with a 7:3 hexane:ethyl acetate mixture gave the product (1.2 g, 80.5%), m.p. 117°-118° C. (ether/hexane). Analytical HPLC showed that the product consisted of two diastereomers in a ratio of 19:1.

후처리

  1. temperatureThe mixture was heated
  2. temperatureat reflux for 1 hour
  3. concentrationconcentrated in vacuo
  4. extractionthe residue extracted with ether
  5. washThe ether extracts were washed with saturated NaHCO3 solution, brine
  6. customdried
  7. concentrationconcentrated in vacuo
  8. washElution from a silica gel column with a 7:3 hexane

출처 및 근거

ORD 기록
ord-03ace325cbc748dd94ba71aeae96dc1e
출처 데이터셋
uspto-grants-1988_05
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US04748252

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