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4-Toluenesulfonyl chloride → 4-[3-(Toluene-4-sulfonyloxymethyl)furan-2-yl]-piperidine-1-carboxylic Acid t-Butyl Ester

HRID 41638
Notes
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Reaction equation

HRID 41638 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([C:14]2[O:15][CH:16]=[CH:17][C:18]=2[CH2:19][OH:20])[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].C1N2CCN(CC2)C1.[S:29](Cl)([C:32]1[CH:38]=[CH:37][C:35]([CH3:36])=[CH:34][CH:33]=1)(=[O:31])=[O:30]>C(Cl)Cl.CCOC(C)=O>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([C:14]2[O:15][CH:16]=[CH:17][C:18]=2[CH2:19][O:20][S:29]([C:32]2[CH:38]=[CH:37][C:35]([CH3:36])=[CH:34][CH:33]=2)(=[O:31])=[O:30])[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 3

HCID 73974-Toluenesulfonyl chlorideHCID 9237DabcoHCID 58442836HCID 58442836, compound

Product 1

HCID 584428304-[3-(Toluene-4-sulfonyloxymethyl)furan-2-yl]-piperidine-1-carboxylic Acid t-Butyl EsterYield 48.6%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolvent
HCID 8857
Ethyl Acetate
Solvent

Conditions

Temperature
0 °C

Procedure

4-(3-Hydroxymethylfuran-2-yl)piperidine-1-carboxylic acid t-butyl ester (0.3 g, 1.1 mmol, 1.0 eq.) was dissolved in DCM (5.7 mL). The mixture was cooled to 0° C. and DABCO (132 mg, 1.2 mmol, 1.1 eq.) was added, followed by TsCl (224 mg, 1.2 mmol, 1.1 eq.). The mixture was stirred at 0° C. for 90 minutes, then diluted with EtOAc (500 mL) and washed with water (2×250 mL). The organic layer was dried over anhydrous Na2SO4, filtered and concentrated by rotary evaporation to yield the title compound (233 mg), which was used without further purification.

Workup

  1. washwashed with water (2×250 mL)
  2. dry with materialThe organic layer was dried over anhydrous Na2SO4
  3. filtrationfiltered
  4. concentrationconcentrated by rotary evaporation

Sources & evidence

ORD record
ord-ba1997f8267f41bdbd91c83964a90e0e
Source dataset
uspto-grants-2013_09
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08530663B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes