Bicarbonate Ion → HCID 11617867、化合物

HRID 2235264ノート

反応式

HRID 2235264 の反応式
Br[C:2]1[CH:20]=[CH:19][CH:18]=[C:17]([Cl:21])[C:3]=1[CH2:4][CH:5]1[CH2:9][CH2:8][N:7]([CH:10]2[CH2:15][CH2:14][CH2:13][CH2:12][CH2:11]2)[C:6]1=[O:16].C([O-])([O-])=O.[Cs+].[Cs+].C(=O)(O)[O-]>C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2]>[CH2:4]([C:2]1[CH:20]=[CH:19][CH:18]=[C:17]([Cl:21])[C:3]=1[CH2:4][CH:5]1[CH2:9][CH2:8][N:7]([CH:10]2[CH2:15][CH2:14][CH2:13][CH2:12][CH2:11]2)[C:6]1=[O:16])[C:3]1[CH:17]=[CH:18][CH:19]=[CH:20][CH:2]=1

参加物

5

反応物 3

HCID 769Bicarbonate IonHCID 10796Cesium carbonateHCID 11632109HCID 11632109、化合物

生成物 1

HCID 11617867HCID 11617867、化合物収率 121.1%

試薬・触媒・溶媒 1

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)触媒

実験手順

Charge a flask with 3-(2-bromo-6-chloro-benzyl)-1-cyclohexyl-pyrrolidin-2-one (Example 56) (250 mg, 0.67 mmol), Pd(dppf)Cl2 (54 mg, 0.067 mmol) and Cs2CO3 (660 mg, 2.0 mmol) and purge with nitrogen. Add DMF (6 mL) and water (0.6 mL) and stir. Add Bn-9-BBN (0.5 M, 4.0 mL, 2.0 mmol) and heat to 60° C. for 1 hour. Pour into saturated aqueous bicarbonate and extract with methylene chloride. Dry over sodium sulfate, filter and concentrate. Purify over silica gel (10% ethyl acetate in hexanes) to yield 155 mg (60%) of the title compound as a clear colorless oil. Mass spectrum (apci) m/z=382.3 (M+H).

後処理

  1. custompurge with nitrogen
  2. extractionextract with methylene chloride
  3. dry with materialDry over sodium sulfate
  4. filtrationfilter
  5. concentrationconcentrate
  6. customPurify over silica gel (10% ethyl acetate in hexanes)

出典と根拠

ORDレコード
ord-c8b3f0e00bfb4b2d9943539213be002b
出典データセット
uspto-grants-2010_05
特許番号
US07713979B2

反応ノート

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