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Water → 1-((S)-7-Fluoro-2,3-dihydrobenzo[1,4]dioxin-2-ylmethyl)-3-methyl-3-[(S)-2-(tetrahydropyran-2-yloxy)ethoxymethyl]piperidine

HRID 453821
Notes
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Reaction equation

HRID 453821 reaction equation
[CH3:1][C@:2]1([CH2:8][O:9][CH2:10][CH2:11][O:12][CH:13]2[CH2:18][CH2:17][CH2:16][CH2:15][O:14]2)[CH2:7][CH2:6][CH2:5][NH:4][CH2:3]1.[F:19][C:20]1[CH:21]=[CH:22][C:23]2[O:28][CH2:27][C@H:26]([CH2:29]OS(C)(=O)=O)[O:25][C:24]=2[CH:35]=1.C([O-])([O-])=O.[K+].[K+].O>CN(C=O)C>[F:19][C:20]1[CH:21]=[CH:22][C:23]2[O:28][CH2:27][C@H:26]([CH2:29][N:4]3[CH2:5][CH2:6][CH2:7][C:2]([CH3:1])([CH2:8][O:9][CH2:10][CH2:11][O:12][C@H:13]4[CH2:18][CH2:17][CH2:16][CH2:15][O:14]4)[CH2:3]3)[O:25][C:24]=2[CH:35]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 66727215(S)-3-Methyl-3-[2-(tetrahydropyran-2-yloxy)ethoxymethyl]piperidineHCID 86644722methanesulfonic acid (R)-(7-fluoro-2,3-dihydrobenzo[1,4]dioxin-2-yl)methyl ester

Product 1

HCID 667268271-((S)-7-Fluoro-2,3-dihydrobenzo[1,4]dioxin-2-ylmethyl)-3-methyl-3-[(S)-2-(tetrahydropyran-2-yloxy)ethoxymethyl]piperidine
Yield 23.6%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

(S)-3-Methyl-3-[2-(tetrahydropyran-2-yloxy)ethoxymethyl]piperidine (100 mg, 0.39 mmol), methanesulfonic acid (R)-(7-fluoro-2,3-dihydrobenzo[1,4]dioxin-2-yl)methyl ester (102 mg, 0.39 mmol), K2CO3 (59 mg, 0.43 mmol) and KI (3 mg) were refluxed in dry DMF (3 ml) for 5 h. Water was added to the cooled mixture, followed by extraction with EtOAc (3×15 ml). The extracts were washed several times with water and finally with brine. After drying and filtering, the solvent was evaporated to give 143 mg of the crude product. This was chromatographed on silica (heptane/EtOAc, 70:30) to give 39 mg of the title compound as a colorless oil.

Workup

  1. extractionfollowed by extraction with EtOAc (3×15 ml)
  2. washThe extracts were washed several times with water
  3. customAfter drying
  4. filtrationfiltering
  5. customthe solvent was evaporated
  6. customto give 143 mg of the crude product
  7. customThis was chromatographed on silica (heptane/EtOAc, 70:30)

Sources & evidence

ORD record
ord-145eaee7bb3d4f27bb3b3f00285d86d2
Source dataset
uspto-grants-2013_07
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08492549B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes