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

HRID 2366018Notes

Reaction equation

HRID 2366018 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-8d670677a1fb4639809f7d4b0b287821
Source dataset
uspto-grants-2014_04
Patent number
US08697723B2

Reaction notes

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