L-Tartaric acid → HCID 24997355, compound

HRID 2421505Notes

Reaction equation

HRID 2421505 reaction equation
[NH2:1][C@:2]1([C:15]#[N:16])[CH2:6][CH2:5][C@@H:4]([C:7]2[CH:12]=[CH:11][C:10]([O:13][CH3:14])=[CH:9][CH:8]=2)[CH2:3]1.N[C@@]1(C#N)CC[C@@H](C2C=CC(OC)=CC=2)C1.[C:33]([OH:42])(=[O:41])[C@@H:34]([C@H:36]([C:38]([OH:40])=[O:39])[OH:37])[OH:35]>CO>[OH:37][C@H:36]([C@@H:34]([OH:35])[C:33]([OH:42])=[O:41])[C:38]([OH:40])=[O:39].[NH2:1][C@:2]1([C:15]#[N:16])[CH2:6][CH2:5][C@@H:4]([C:7]2[CH:12]=[CH:11][C:10]([O:13][CH3:14])=[CH:9][CH:8]=2)[CH2:3]1

Participants

5

Reactant 3

HCID 444305L-Tartaric acidHCID 24997356HCID 24997356, compoundHCID 25001773HCID 25001773, compound

Product 1

HCID 24997355HCID 24997355, compoundYield 28%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

The mixture of (1R,3R)-1-Amino-3-(4-methoxy-phenyl)-cyclopentanecarbonitrile and (1S,3R)-1-Amino-3-(4-methoxy-phenyl)-cyclopentanecarbonitrile (12.4 g), from Exemplification H1, was dissolved in methanol (100 ml) and added to a solution of L-Tartaric acid (8.69 g, 57.9 mmol) in methanol (100 ml). The resulting solid was filtered off and triturated repeatedly with 80 ml portions of methanol until the more soluble isomer was very nearly gone as indicated by HPLC (ThermoQuest 50×4.6 mm, 5 u, Hypercarb column, part # 35005-025). The remaining white solid was dried to yield 6.0 g (28%) of (1R,3R)-1-Amino-3-(4-methoxy-phenyl)-cyclopentanecarbonitrile; compound with (2R,3R)-2,3-dihydroxy-succinic acid. NMR (DMSO-d6) 7.18 (d, 2H), 6.85 (d, 2H), 4.22 (s, 2H), 3.72 (s, 3H), 3.30-3.41 (m, 1H), 2.10-2.30 (m, 3H), 1.8-2.0 (m, 2H), 1.6-1.75 (m, 1H), LCMS (ELSD) no parent ion, Rt=2.26 min

Workup

  1. filtrationThe resulting solid was filtered off
  2. customtriturated repeatedly with 80 ml portions of methanol until the more soluble isomer
  3. customThe remaining white solid was dried

Sources & evidence

ORD record
ord-a9dc66068be443b9b574ba11e78f2f22
Source dataset
uspto-grants-2011_06
Patent number
US07956195B2

Reaction notes

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