Lithium diisopropylamide → HCID 86757639, compound

HRID 2268167Notes

Reaction equation

HRID 2268167 reaction equation
[CH3:1][O:2][C:3]1[C:11]2[O:10][N:9]=[C:8]([CH3:12])[C:7]=2[CH:6]=[CH:5][CH:4]=1.IC[CH:15]1[CH2:20][CH2:19][N:18]([C:21]([O:23][C:24]([CH3:27])([CH3:26])[CH3:25])=[O:22])[CH2:17][CH2:16]1.[Li+].[CH3:29]C([N-]C(C)C)C>C1COCC1>[CH3:1][O:2][C:3]1[C:11]2[O:10][N:9]=[C:8]([CH2:12][CH2:29][CH:17]3[CH2:16][CH2:15][CH2:20][CH2:19][N:18]3[C:21]([O:23][C:24]([CH3:25])([CH3:26])[CH3:27])=[O:22])[C:7]=2[CH:6]=[CH:5][CH:4]=1

Participants

5

Reactant 3

HCID 2724682Lithium diisopropylamideHCID 10448961Tert-butyl 4-(iodomethyl)piperidine-1-carboxylateHCID 18377512HCID 18377512, compound

Product 1

HCID 86757639HCID 86757639, compoundYield 62%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

The procedure described in Example 1d was followed using 7-methoxy-3-methyl-1,2-benzisoxazole (0.30 g, 1.84 mmol), 4-iodomethyl-1-piperidinecarboxylic acid, 1-(1,1-dimethylethyl) ester (0.60 g, 1.85 mmol), and 1M LDA (1.9 mL, 1.9 mmol) in dry THF (2 mL). After purification, the title compound (0.41 g, 62%) was obtained as a pale yellow oil.

Workup

  1. customAfter purification

Sources & evidence

ORD record
ord-ac41ca8892f4420bb46e70087825a4d8
Source dataset
uspto-grants-2001_12
Patent number
US06326382B1

Reaction notes

Loading…