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ethyl 3-(2-chloro-6-morpholino-9H-purin-9-yl)propanoate → 1-(2-(2-chloro-6-morpholino-9H-purin-9-yl)ethyl)cyclopropanol

HRID 334124
Notes
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Reaction equation

HRID 334124 reaction equation
[Cl:1][C:2]1[N:10]=[C:9]2[C:5]([N:6]=[CH:7][N:8]2[CH2:11][CH2:12][C:13](OCC)=[O:14])=[C:4]([N:18]2[CH2:23][CH2:22][O:21][CH2:20][CH2:19]2)[N:3]=1.[CH2:24]([Mg]Br)[CH3:25]>C(OCC)C.[O-]CC.[Ti+4].[O-]CC.[O-]CC.[O-]CC>[Cl:1][C:2]1[N:10]=[C:9]2[C:5]([N:6]=[CH:7][N:8]2[CH2:11][CH2:12][C:13]2([OH:14])[CH2:25][CH2:24]2)=[C:4]([N:18]2[CH2:19][CH2:20][O:21][CH2:22][CH2:23]2)[N:3]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 2

HCID 86667344ethyl 3-(2-chloro-6-morpholino-9H-purin-9-yl)propanoateHCID 178418443HCID 178418443, compound2×

Product 1

HCID 866673431-(2-(2-chloro-6-morpholino-9H-purin-9-yl)ethyl)cyclopropanolYield 46%

Reagents, catalysts & solvents 2

HCID 76524Titanium tetraethoxideCatalyst2×
HCID 3283
Diethyl Ether
Solvent
3×

Procedure

A solution of ethyl 3-(2-chloro-6-morpholino-9H-purin-9-yl)propanoate (500 mg, 1.5 mmol) in diethylether (37 mL) was treated with titanium (IV) ethoxide (31 uL, 0.15 mmol) followed by the dropwise addition of 3.0M ethylmagnesium bromide in ether (0.98 mL, 2.9 mmol) at ambient temperature for 90 minutes. Partial conversion prompted the addition of titanium (IV) ethoxide (31 uL, 0.15 mmol) and 3.0M ethylmagnesium bromide in ether (0.98 mL, 2.9 mmol). After 2 hr, the reaction mixture was quenched with an aqueous 1.0M solution of HCl (20 mL) and filtered through a plug of celite, washing with ethyl acetate. The mixture was diluted with water and ethyl acetate and the layers separated. The aqueous phase was extracted into EtOAc (3×), dried over sodium sulfate, filtered, and absorbed onto celite for purification by flash chromatography to afford 1-(2-(2-chloro-6-morpholino-9H-purin-9-yl)ethyl)cyclopropanol as a colorless oil (220 mg, 46%). LC/MS (ESI+): m/z 324 (M+H)

Workup

  1. customthe reaction mixture was quenched with an aqueous 1.0M solution of HCl (20 mL)
  2. filtrationfiltered through a plug of celite
  3. washwashing with ethyl acetate
  4. additionThe mixture was diluted with water and ethyl acetate
  5. customthe layers separated
  6. extractionThe aqueous phase was extracted into EtOAc (3×)
  7. dry with materialdried over sodium sulfate
  8. filtrationfiltered
  9. customabsorbed onto celite for purification by flash chromatography

Sources & evidence

ORD record
ord-ec47c2b20fdf47d4aef5d2f98ce27b95
Source dataset
uspto-grants-2014_11
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08883799B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes