Piperidine → 5-Chloro-3H-spiro[1-benzofuran-2,3'-pyrrolidine]

HRID 270099Notes

Reaction equation

HRID 270099 reaction equation
N1CCCCC1.C([N:14]1[CH2:18][CH2:17][C:16]2([CH2:22][C:21]3[CH:23]=[C:24]([Cl:27])[CH:25]=[CH:26][C:20]=3[O:19]2)[CH2:15]1)C1C=CC=CC=1.ClC(OCC)=O.[OH-].[K+]>ClCCl.[OH-].[NH4+].CO.C(O)C.O.C1(C)C=CC=CC=1>[Cl:27][C:24]1[CH:25]=[CH:26][C:20]2[O:19][C:16]3([CH2:17][CH2:18][NH:14][CH2:15]3)[CH2:22][C:21]=2[CH:23]=1

Participants

11

Reactant 4

HCID 8082PiperidineHCID 10928Ethyl chloroformateHCID 14797Potassium HydroxideHCID 59833627HCID 59833627, compound

Product 1

HCID 598336445-Chloro-3H-spiro[1-benzofuran-2,3'-pyrrolidine]Yield 61.9%

Reagents, catalysts & solvents 6

HCID 702EthanolSolventHCID 887MethanolSolventHCID 962WaterSolventHCID 1140TolueneSolventHCID 6344DichloromethaneSolventHCID 14923Ammonium HydroxideSolvent2×

Procedure

The experimental procedure is the same as described above for the corresponding piperidine derivative using 1′-benzyl-5-chloro-3H-spiro[1-benzofuran-2,3′-pyrrolidine] (555 mg, 1.85 mmol), ethyl chloroformate (261 mg, 2.4 mmol), toluene (5 mL), potassium hydroxide (KOH) (3.0 g), water (3 mL) and ethanol (6 mL) to give the titled compound (240 mg) after silica gel flash chromatography (0-2% methanol in dichloromethane, 0.2% ammonium hydroxide, NH4OH).

Sources & evidence

ORD record
ord-109f89a5cf3948b0b4c12fae8e67f820
Source dataset
uspto-grants-2008_11
Patent number
US07449475B2

Reaction notes

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