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Water → 5-((Bis(4-methoxyphenyl)(phenyl)methoxy)methyl)pyrrolidin-3-ol

HRID 2407049
Notes
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Reaction equation

HRID 2407049 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]([C:41]2[CH:46]=[CH:45][C:44]([O:47][CH3:48])=[CH:43][CH:42]=2)([C:35]2[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=2)[O:10][CH2:11][CH:12]2[CH2:16][CH:15]([OH:17])[CH2:14][N:13]2C(OCC2C3C=CC=CC=3C3C2=CC=CC=3)=O)=[CH:5][CH:4]=1.N1CCCCC1.O.C(OCC)(=O)C>CN(C)C=O>[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]([C:9]([C:41]2[CH:42]=[CH:43][C:44]([O:47][CH3:48])=[CH:45][CH:46]=2)([C:35]2[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=2)[O:10][CH2:11][CH:12]2[NH:13][CH2:14][CH:15]([OH:17])[CH2:16]2)=[CH:7][CH:8]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 962WaterHCID 8082PiperidineHCID 8857Ethyl AcetateHCID 69094046(9H-fluoren-9-yl)methyl 2-((bis(4-methoxyphenyl)(phenyl)-methoxy)methyl)-4-hydroxypyrrolidine-1-carboxylate

Product 1

HCID 234051185-((Bis(4-methoxyphenyl)(phenyl)methoxy)methyl)pyrrolidin-3-ol

Reagents, catalysts & solvents 1

HCID 6228
Dimethylformamide
Solvent

Procedure

(9H-Fluoren-9-yl)methyl 2-((bis(4-methoxyphenyl)(phenyl)-methoxy)methyl)-4-hydroxypyrrol-idine-1-carboxylate (3.4 g, 5.3 mmoles) is dissolved in anhydrous N,N-dimethylformamide (15 mL). The solution is stirred at ambient temperature, and piperidine (1.1 mL, 11. mmoles) is added. After 1 hour, a copious white precipitate has formed. Water (100 mL) and ethyl acetate (75 mL) are added, and the mixture is stirred until all of the solid has dissolved. The layers are separated and the aqueous layer is extracted with ethyl acetate (75 mL). The combined ethyl acetate layers are washed with saturated aqueous sodium bicarbonate (50 mL) then saturated aqueous sodium chloride (50 mL), dried over anhydrous sodium sulfate and filtered. The filtrate is evaporated to an amorphous white solid. The crude product is purified on silica gel (150 mL bed volume) eluting with methylene chloride:methanol:triethylamine (94:1:5 [v/v/v], 700 mL; then 90:5:5 [v/v/v], 700 mL). Fractions containing pure product by thin layer chromatography are pooled and evaporated to a white glassy foam, which is dried well in vacuo. The yield is 2.2 g (99%).

Workup

  1. customa copious white precipitate has formed
  2. stirringthe mixture is stirred until all of the solid
  3. dissolutionhas dissolved
  4. customThe layers are separated
  5. extractionthe aqueous layer is extracted with ethyl acetate (75 mL)
  6. washThe combined ethyl acetate layers are washed with saturated aqueous sodium bicarbonate (50 mL)
  7. dry with materialsaturated aqueous sodium chloride (50 mL), dried over anhydrous sodium sulfate
  8. filtrationfiltered
  9. customThe filtrate is evaporated to an amorphous white solid
  10. customThe crude product is purified on silica gel (150 mL bed volume)
  11. washeluting with methylene chloride:methanol:triethylamine (94:1:5 [v/v/v], 700 mL
  12. additionFractions containing pure product by thin layer chromatography
  13. customevaporated to a white glassy foam, which
  14. customis dried well in vacuo

Sources & evidence

ORD record
ord-4af66f4e08454ea98a311d2cd1ab48fc
Source dataset
uspto-grants-2014_08
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08809514B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes