Bicarbonate Ion → HCID 11617867, 화합물

HRID 2235264노트

반응식

HRID 2235264 반응식
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

참가 물질

5

반응물 3

HCID 769Bicarbonate IonHCID 10796Cesium carbonateHCID 11632109HCID 11632109, 화합물

생성물 1

HCID 11617867HCID 11617867, 화합물수율 121.1%

시약·촉매·용매 1

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

실험 절차

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).

후처리

  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)

출처 및 근거

ORD 기록
ord-c8b3f0e00bfb4b2d9943539213be002b
출처 데이터셋
uspto-grants-2010_05
특허 번호
US07713979B2

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