Dibenzoyl-L-tartaric acid → HCID 59600241, compound

HRID 2267689Notes

Reaction equation

HRID 2267689 reaction equation
[CH3:1][C@H:2]1[C@H:7]([O:8][C:9](=[O:14])[C:10]([CH3:13])([CH3:12])[CH3:11])[CH2:6][CH2:5][NH:4][CH2:3]1.C1C=CC(C(O[C@@H](C(O)=O)[C@@H](OC(C2C=CC=CC=2)=O)C(O)=O)=O)=CC=1>CCOC(C)=O>[CH3:1][C@@H:2]1[C@@H:7]([O:8][C:9](=[O:14])[C:10]([CH3:13])([CH3:12])[CH3:11])[CH2:6][CH2:5][NH:4][CH2:3]1

Participants

4

Reactant 2

HCID 75969Dibenzoyl-L-tartaric acidHCID 59600263(3R,4R)-3-methylpiperidin-4-yl pivalate

Product 1

HCID 59600241HCID 59600241, compound

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent2×

Procedure

Racemic 19 (62.7 g, 314.4 mmol) is dissolved in EtOAc (300 ml) and a solution of L-(−)-O,O′-Dibenzoyl tartaric acid (56.3 g, 157.2 mmol) in EtOAc (450 ml) is added. The formed solid is filtered off, washed with cold EtOAc and dried. It is then re-crystallized from hot methanol (400 ml). The crystals are collected and the free base is liberated by treatment with 1N—NaOH and extraction with ether.

Workup

  1. filtrationThe formed solid is filtered off
  2. washwashed with cold EtOAc
  3. customdried
  4. customIt is then re-crystallized from hot methanol (400 ml)
  5. customThe crystals are collected
  6. extractionthe free base is liberated by treatment with 1N—NaOH and extraction with ether

Sources & evidence

ORD record
ord-0978a5f09a774926a4307b02f9b62a0f
Source dataset
uspto-grants-2010_12
Patent number
US07858781B2

Reaction notes

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