Water → HCID 68502963, compound

HRID 2354112Notes

Reaction equation

HRID 2354112 reaction equation
[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]

Participants

6

Reactant 4

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

Product 1

HCID 68502963HCID 68502963, compoundYield 79%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-9dbe5d24ebd24e8282f9bc22d507ab00
Source dataset
uspto-grants-2010_07
Patent number
US07750167B2

Reaction notes

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