Lithium Hydroxide → Lithium (S)-1-[(S)-1-(2,3-dihydrobenzo[1,4]dioxin-2-yl)methyl]-3-methyl-piperidine-3-carboxylate

HRID 453810Notes

Reaction equation

HRID 453810 reaction equation
C([O:3][C:4]([C@@:6]1([CH3:24])[CH2:11][CH2:10][CH2:9][N:8]([C:12]([C@@H:14]2[O:19][C:18]3[CH:20]=[CH:21][CH:22]=[CH:23][C:17]=3[O:16][CH2:15]2)=O)[CH2:7]1)=[O:5])C.[OH-].[Li+:26].C1COCC1>O>[O:19]1[C:18]2[CH:20]=[CH:21][CH:22]=[CH:23][C:17]=2[O:16][CH2:15][C@@H:14]1[CH2:12][N:8]1[CH2:9][CH2:10][CH2:11][C@:6]([CH3:24])([C:4]([O-:5])=[O:3])[CH2:7]1.[Li+:26]

Participants

5

Reactant 3

HCID 3939Lithium HydroxideHCID 8028TetrahydrofuranHCID 66727067(S)-1-((R)-2,3-Dihydrobenzo[1,4]dioxine-2-carbonyl)-3-methylpiperidine-3-carboxylic acid ethyl ester

Product 1

HCID 66727429Lithium (S)-1-[(S)-1-(2,3-dihydrobenzo[1,4]dioxin-2-yl)methyl]-3-methyl-piperidine-3-carboxylateYield 74.2%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

(S)-1-((R)-2,3-Dihydrobenzo[1,4]dioxine-2-carbonyl)-3-methylpiperidine-3-carboxylic acid ethyl ester (512 mg, 1.60 mmol), 1 M lithium hydroxide (4.81 ml, 4.81 mmol) and THF:H2O solution (9:1) (5 ml) were heated under microwaves at 100° C. for 26 h. The mixture was filtered and evaporated to dryness. The residue was dissolved in water and washed twice with EtOAc and the aqueous phase was evaporated to dryness to give 353 mg of the title compound.

Workup

  1. filtrationThe mixture was filtered
  2. customevaporated to dryness
  3. dissolutionThe residue was dissolved in water
  4. washwashed twice with EtOAc
  5. customthe aqueous phase was evaporated to dryness

Sources & evidence

ORD record
ord-1f4d85208ed34c7898b03ae08147e4bb
Source dataset
uspto-grants-2013_07
Patent number
US08492549B2

Reaction notes

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