Dichloromethane → HCID 71652161, compound

HRID 1426368Notes

Reaction equation

HRID 1426368 reaction equation
[CH2:1]1[C:5]2[CH:6]=[CH:7][C:8]([O:10][CH2:11][C@H:12]3[C@H:17]([C:18]4[CH:23]=[CH:22][C:21]([F:24])=[CH:20][CH:19]=4)[CH2:16][CH2:15][N:14](C(OC(C)(C)C)=O)[CH2:13]3)=[CH:9][C:4]=2[CH2:3][O:2]1.FC(F)(F)C(O)=O.ClCCl>C1(C)C=CC=CC=1>[CH2:1]1[C:5]2[CH:6]=[CH:7][C:8]([O:10][CH2:11][C@H:12]3[C@H:17]([C:18]4[CH:19]=[CH:20][C:21]([F:24])=[CH:22][CH:23]=4)[CH2:16][CH2:15][NH:14][CH2:13]3)=[CH:9][C:4]=2[CH2:3][O:2]1

Participants

5

Reactant 3

HCID 6344DichloromethaneHCID 6422Trifluoroacetic acidHCID 86691228HCID 86691228, compound

Product 1

HCID 71652161HCID 71652161, compoundYield 85.9%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

To tert-butyl (3S,4R)-3-[(1,3-dihydro-2-benzofuran-5-yloxy)methyl]-4-(4-fluorophenyl)piperidine-1-carboxylate (4.1 g, 9.6 mmol) described in Production Example 1-4 was added a mixed solution of trifluoroacetic acid (5 mL) and dichloromethane (30 mL) under ice cooling, followed by stirring at room temperature for 90 minutes. Toluene (30 mL) was added to the reaction mixture, and the solvent was distilled away under reduced pressure. The residue was purified by NH silica gel column chromatography (methanol:ethyl acetate=1:20) to give the title compound (2.7 g, 84% yield).

Workup

  1. distillationthe solvent was distilled away under reduced pressure
  2. customThe residue was purified by NH silica gel column chromatography (methanol:ethyl acetate=1:20)

Sources & evidence

ORD record
ord-0c09924ccca747e4abcb7157e4f83809
Source dataset
uspto-grants-2015_01
Patent number
US08933100B2

Reaction notes

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