反应 #1328411

ord-50f534378dfb43568c08aa0ecd0fbed0

反应方程式

O=C1c2ccccc2C(=O)N1[C@H](CI)Cc1c[nH]c2c(OCc3ccccc3)cccc12
(S)-7-benzyloxy-3-(3-iodo-2-phthalimidopropyl)indole
O=C([O-])[O-].[K+].[K+]
potassium carbonate
O=C[O-].[NH4+]
ammonium formate
C[C@H](Cc1c[nH]c2c(OCc3ccccc3)cccc12)N1C(=O)c2ccccc2C1=O
title compound
收率 79.4%
C[C@H](Cc1c[nH]c2c(OCc3ccccc3)cccc12)N1C(=O)c2ccccc2C1=O
(R)-7-benzyloxy-3-(2-phthalimidopropyl)indole
收率 79.4%

溶剂

反应条件

温度
85°CELSIUS
详细条件
See reaction.notes.procedure_details.

后处理

  1. 1
    workup.ADDITIONAdded
  2. 2
    温度After cooling down
  3. 3
    过滤the catalyst was filtered off
  4. 4
    workup.ADDITIONthe filtrate was diluted with ethyl acetate
  5. 5
    workup.ADDITIONThen, water was added
  6. 6
    其他the organic layer was separated
  7. 7
    洗涤The organic layer was washed in order with a 10% sodium thiosulfate aqueous solution
  8. 8
    干燥a sodium hydroxide aqueous solution, hydrochloric acid and a saturated sodium chloride aqueous solution, and then it was dried
  9. 9
    过滤filtered
  10. 10
    浓缩concentrated under reduced pressure

实验过程

A 10% palladium on carbon catalyst (content 50%) 4.00 g was suspended in 200 ml of DMF, and 20.00 g of (S)-7-benzyloxy-3-(3-iodo-2-phthalimidopropyl)indole was added thereto. Added while stirring were 8.00 g of potassium carbonate and 6.00 g of ammonium formate, the suspension was heated in an oil bath of 85° C. For one hour. After cooling down, the catalyst was filtered off, and the filtrate was diluted with ethyl acetate. Then, water was added thereto, and the organic layer was separated. The organic layer was washed in order with a 10% sodium thiosulfate aqueous solution, a sodium hydroxide aqueous solution, hydrochloric acid and a saturated sodium chloride aqueous solution, and then it was dried, filtered and concentrated under reduced pressure, whereby 12.16 g of the title compound was obtained in the form of a yellow amorphous solid shaped substance.

来源

DOI: 10.6084/m9.figshare.5104873.v1专利: US07115412B2uspto-grants-2006_10