Lithium diisopropylamide → 4-[2-[5,6-Dimethyl-1,2-benzisoxazol-3-yl]ethyl]-1-piperidinecarboxylic acid, 1-(1,1-dimethylethyl) ester

HRID 2268164Notes

Reaction equation

HRID 2268164 reaction equation
[CH3:1][C:2]1[C:6]2[CH:7]=[C:8]([CH3:12])[C:9]([CH3:11])=[CH:10][C:5]=2[O:4][N:3]=1.I[CH2:14][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+].CC([N-]C(C)C)C>C1COCC1>[CH3:12][C:8]1[C:9]([CH3:11])=[CH:10][C:5]2[O:4][N:3]=[C:2]([CH2:1][CH2:14][CH:15]3[CH2:20][CH2:19][N:18]([C:21]([O:23][C:24]([CH3:25])([CH3:27])[CH3:26])=[O:22])[CH2:17][CH2:16]3)[C:6]=2[CH:7]=1

Participants

5

Reactant 3

HCID 2724682Lithium diisopropylamideHCID 10448961Tert-butyl 4-(iodomethyl)piperidine-1-carboxylateHCID 123854753,5,6-Trimethylbenzo[d]isoxazole

Product 1

HCID 102478404-[2-[5,6-Dimethyl-1,2-benzisoxazol-3-yl]ethyl]-1-piperidinecarboxylic acid, 1-(1,1-dimethylethyl) esterYield 78%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

The procedure described in Example 1d was followed using 3,5,6-trimethyl-1,2-benzisoxazole (0.600 g, 3.73 mmol), 4-iodomethyl-1-piperidinecarboxylic acid, 1-(1,1-dimethylethyl) ester (1.30 g, 4.10 mmol), and 1M LDA (4.10 mL, 4.10 mmol) in dry THF (10 mL). After purification, the title compound (1.04 g, 78%) was obtained as a clear oil.

Workup

  1. customAfter purification

Sources & evidence

ORD record
ord-ea0ffddbdf42435bb5b6f7ec14c7f3bb
Source dataset
uspto-grants-2001_12
Patent number
US06326382B1

Reaction notes

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