Water → HCID 68502963、化合物

HRID 2354112ノート

反応式

HRID 2354112 の反応式
[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]

参加物

6

反応物 4

HCID 962WaterHCID 2724682Lithium diisopropylamideHCID 21263495Tetrahydrofuran heptaneHCID 25178693HCID 25178693、化合物

生成物 1

HCID 68502963HCID 68502963、化合物収率 79%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-9dbe5d24ebd24e8282f9bc22d507ab00
出典データセット
uspto-grants-2010_07
特許番号
US07750167B2

反応ノート

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