HCID 70239410, compound → HCID 70239495, compound

HRID 565725Notes

Reaction equation

HRID 565725 reaction equation
[CH3:1][C@H:2]([N:9]1[CH2:18][CH2:17][CH2:16][CH2:15][CH:10]1[C:11]([O:13][CH3:14])=[O:12])[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1>C(OC)(C)(C)C>[CH3:1][C@H:2]([N:9]1[CH2:18][CH2:17][CH2:16][CH2:15][C@H:10]1[C:11]([O:13][CH3:14])=[O:12])[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1

Participants

3

Reactant 1

HCID 70239410HCID 70239410, compound

Product 1

HCID 70239495HCID 70239495, compoundYield 44.5%

Reagents, catalysts & solvents 1

HCID 15413tert-Butyl methyl etherSolvent2×

Procedure

Methyl N-[(S)-α-methylbenzyl]-(RS)-pipecolate (159 mg) was dissolved in methyl tert-butyl ether (2 ml) at room temperature. To this solution was added a mixture of (2S)-L-(−)-malic acid (120 mg) and methyl tert-butyl ether (2 ml) at room temperature and stirred. The resultant solution was allowed to stand at −20° C. for one day to form crystals. The crystals were separated by filtration and dried to yield a (2S)-L-(−)-malic acid salt of methyl N-[(S)-α-methylbenzyl]-(S)-pipecolate (70.8 mg) in an optical purity of 41% de and a yield of 29%.

Workup

  1. additionTo this solution was added
  2. customto form crystals
  3. customThe crystals were separated by filtration
  4. customdried

Sources & evidence

ORD record
ord-78d36c8b531a440c8d756829a907aed4
Source dataset
uspto-grants-2001_01
Patent number
US06172234B2

Reaction notes

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