Dibenzoyl-L-tartaric acid → HCID 59600241, compound

HRID 1928989Notes

Reaction equation

HRID 1928989 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-(−)-0,0′-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-95dcb244d7b34331b9fed35d1657614f
Source dataset
uspto-grants-2012_05
Patent number
US08183366B2

Reaction notes

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