Water → (1S,2R,4S)-4-(dibenzylamino)-2-methylcyclopentanecarboxylic acid

HRID 1969573Notes

Reaction equation

HRID 1969573 reaction equation
P(=O)(O)(O)O.O.[CH2:7]([N:14]([CH2:24][C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1)[C@@H:15]1[CH2:19][C@H:18]([C:20]([O-:22])=[O:21])[C@H:17]([CH3:23])[CH2:16]1)[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1.C1([C@H](N)C)C=CC=CC=1>CC(OC)(C)C>[CH2:24]([N:14]([CH2:7][C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C@@H:15]1[CH2:19][C@H:18]([C:20]([OH:22])=[O:21])[C@H:17]([CH3:23])[CH2:16]1)[C:25]1[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=1

Participants

5

Reactant 3

HCID 962WaterHCID 1004Phosphoric AcidHCID 86761815(1S,2R,4S)-4-(dibenzylamino)-2-methylcyclopentanecarboxylate.(R)-1-phenylethanamine

Product 1

HCID 58557217(1S,2R,4S)-4-(dibenzylamino)-2-methylcyclopentanecarboxylic acidYield 99.2%

Reagents, catalysts & solvents 1

HCID 15413tert-Butyl methyl etherSolvent

Procedure

Phosphoric acid (11.40 mL, 196 mmol) was added to a flask containing water (500 mL). The solution was stirred for about 5 min. (1S,2R,4S)-4-(dibenzylamino)-2-methylcyclopentanecarboxylate•(R)-1-phenylethanamine (83 g, 187 mmol) was added to the solution in small portions. MTBE (500 mL) was added and the contents were mixed well, dissolving the solid. The phases were settled and separated. The aqueous layer was back extracted with MTBE (150 mL). The combined organic phases were dried over anhydrous sodium sulfate, filtered, and concentrated in vacuo to afford (1S,2R,4S)-4-(dibenzylamino)-2-methylcyclopentanecarboxylic acid (60 g, 99%) as an oil: HPLC (Table 1, Method x) Rt=4.57 min.

Workup

  1. additionwas added to the solution in small portions
  2. additionthe contents were mixed well
  3. dissolutiondissolving the solid
  4. customseparated
  5. extractionThe aqueous layer was back extracted with MTBE (150 mL)
  6. dry with materialThe combined organic phases were dried over anhydrous sodium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-02598564fd564f9a9f415a53d9c5ae82
Source dataset
uspto-grants-2013_04
Patent number
US08426411B2

Reaction notes

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