Water → HCID 67324298, compound

HRID 1401828Notes

Reaction equation

HRID 1401828 reaction equation
Br.C([O:4][C:5]([CH:7]1[CH2:12][CH2:11][N:10]([C:13]2[S:14][CH:15]=[C:16]([C:18]3[CH:27]=[CH:26][C:25]4[C:24]([CH3:29])([CH3:28])[CH2:23][CH2:22][C:21]([CH3:31])([CH3:30])[C:20]=4[CH:19]=3)[N:17]=2)[CH2:9][CH2:8]1)=[O:6])C.O.[OH-].[Li+]>C1COCC1>[CH3:28][C:24]1([CH3:29])[CH2:23][CH2:22][C:21]([CH3:30])([CH3:31])[C:20]2[CH:19]=[C:18]([C:16]3[N:17]=[C:13]([N:10]4[CH2:11][CH2:12][CH:7]([C:5]([OH:6])=[O:4])[CH2:8][CH2:9]4)[S:14][CH:15]=3)[CH:27]=[CH:26][C:25]1=2

Participants

5

Reactant 3

HCID 962WaterHCID 3939Lithium HydroxideHCID 68381189HCID 68381189, compound

Product 1

HCID 67324298HCID 67324298, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

3.5 g (6.90 mmol) of 1-[4-(5,5,8,8-tetramethyl-5,6,7,8-tetrahydronaphthalen-2-yl)thiazol-2-yl]piperidine-4-carboxylic acid ethyl ester hydrobromide from step a were slurried in 25 ml of THF, 21 ml of water and 843 mg (34.48 mmol) of lithium hydroxide were added, and the mixture was stirred at room temperature overnight. The reaction mixture was evaporated in a rotary evaporator, adjusted to pH=1 using a 1N hydrochloric acid solution and then extracted twice with EA. The combined organic phases were dried over sodium sulfate, filtered and evaporated.

Workup

  1. customThe reaction mixture was evaporated in a rotary evaporator
  2. extractionextracted twice with EA
  3. dry with materialThe combined organic phases were dried over sodium sulfate
  4. filtrationfiltered
  5. customevaporated

Sources & evidence

ORD record
ord-1f1125edd99f4b64ade19259fc459fd7
Source dataset
uspto-grants-2014_12
Patent number
US08907098B2

Reaction notes

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