Lithium diisopropylamide → HCID 10089931, compound

HRID 2268166Notes

Reaction equation

HRID 2268166 reaction equation
[CH3:1][O:2][C:3]1[CH:12]=[CH:11][C:6]2[C:7]([CH3:10])=[N:8][O:9][C:5]=2[CH:4]=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>[CH3:1][O:2][C:3]1[CH:12]=[CH:11][C:6]2[C:7]([CH2:10][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)=[N:8][O:9][C:5]=2[CH:4]=1

Participants

5

Reactant 3

HCID 2724682Lithium diisopropylamideHCID 10448961Tert-butyl 4-(iodomethyl)piperidine-1-carboxylateHCID 126246736-Methoxy-3-methyl-1,2-benzoxazole

Product 1

HCID 10089931HCID 10089931, compoundYield 80.7%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

The procedure described in Example 1d was followed using 6-methoxy-3-methyl-1,2-benzisoxazole (0.32 g, 1.96 mmol), 4-iodomethyl-1-piperidinecarboxylic acid, 1-(1,1-dimethylethyl) ester (0.70 g, 2.15 mmol), and 1M LDA (2.0 mL, 2.0 mmol) in dry THF (3 mL). After purification, the title compound (0.57 g, 80%) was obtained as a white solid.

Workup

  1. customAfter purification

Sources & evidence

ORD record
ord-529e73e23e564e3586967777b7b8c6ee
Source dataset
uspto-grants-2001_12
Patent number
US06326382B1

Reaction notes

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