Water → HCID 68502963, 화합물

HRID 1516872노트

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HRID 1516872 반응식
[Br:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1/[CH:8]=[CH:9]/[C:10]1[CH:15]=[C:14]([Cl:16])[CH:13]=[CH:12][C:11]=1[OH:17].[CH:18]([N-:21][CH:22](C)C)(C)[CH3:19].[Li+].CCCCCCC.C1COCC1.O>O1CCCC1>[CH3:22][N:21]1[CH2:18][CH2:19][C@@H:9]([C:10]2[CH:15]=[C:14]([Cl:16])[CH:13]=[CH:12][C:11]=2[OH:17])[C@@H:8]1[C:3]1[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=1[Br:1]

참가 물질

6

반응물 4

HCID 962WaterHCID 2724682Lithium diisopropylamideHCID 21263495Tetrahydrofuran heptaneHCID 25178693HCID 25178693, 화합물

생성물 1

HCID 68502963HCID 68502963, 화합물수율 79%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

To a solution of trans-2-bromo-5′-chloro-2′-hydroxystilbene (81 g, 261 mmol) in tetrahydrofuran (570 ml) trimethylamine-N-oxide.dihydrate (43.4 g, 390 mmol) was added at ambient temperature. Lithium diisopropylamide in heptane/THF (2M, 1070 ml, 2140 mmol) was then added during the course of 1 hour while maintaining the temperature below 40° C. After completion of the reaction water (120 ml) was added. Solvent was evaporated to a small volume after which ethyl acetate (250 ml) was added. The pH was adjusted to pH 8 with 18% hydrochloric acid (˜250 ml) and ethyl acetate (250 ml) was added. The organic layer was separated and the aqueous layer was again extracted with ethyl acetate (2×120 ml). The combined organic layers were washed with water (325 ml) and with brine, dried (MgSO4) and then evaporated in vacuo. The resulting oil was crystallised from ethanol/water (1/1, v/v) to give the title pyrrolidine (62.0 g, 79%). Purity according to HPLC is 99% a/a.

후처리

  1. temperaturewhile maintaining the temperature below 40° C
  2. additionwas added
  3. customSolvent was evaporated to a small volume after which ethyl acetate (250 ml)
  4. additionwas added
  5. additionwas added
  6. customThe organic layer was separated
  7. extractionthe aqueous layer was again extracted with ethyl acetate (2×120 ml)
  8. washThe combined organic layers were washed with water (325 ml) and with brine
  9. dry with materialdried (MgSO4)
  10. customevaporated in vacuo
  11. customThe resulting oil was crystallised from ethanol/water (1/1

출처 및 근거

ORD 기록
ord-3f85a565563a4190a92062c45a58db0d
출처 데이터셋
uspto-grants-2012_07
특허 번호
US08227623B2

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