L-Tartaric acid → HCID 66997652, compound

HRID 2363454Notes

Reaction equation

HRID 2363454 reaction equation
[CH2:1]([N:8]1[CH2:12][C@@H:11]2[C@@H:13]([NH2:16])[CH2:14][CH2:15][C@@H:10]2[CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:17]([OH:26])(=[O:25])[C@@H:18]([C@H:20]([C:22]([OH:24])=[O:23])[OH:21])[OH:19]>C(O)C>[OH:21][C@H:20]([C@@H:18]([OH:19])[C:17]([OH:26])=[O:25])[C:22]([OH:24])=[O:23].[CH2:1]([N:8]1[CH2:12][C@@H:11]2[C@@H:13]([NH2:16])[CH2:14][CH2:15][C@@H:10]2[CH2:9]1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 444305L-Tartaric acidHCID 66591011(3aR,4S,6aS)-2-benzyloctahydrocyclopenta[c]pyrrol-4-amine

Product 1

HCID 66997652HCID 66997652, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent3×

Procedure

(3aR,4S,6aS)-2-Benzyloctahydrocyclopenta[c]pyrrol-4-amine (1.26 g, 5.82 mmol) from Step 2 and ethanol (12 mL) were combined. L-Tartaric acid in ethanol (4.7 mL) was added to the reaction solution over 2 hours. The resulting slurry was further diluted with ethanol (10 mL). The slurry was filtered and the cake was rinsed with ethanol (10 mL) to provide (3aR,4S,6aS)-2-benzyloctahydrocyclopenta-[c]pyrrol-4-amine(2R,3R)-2,3-dihydroxysuccinate: 1H NMR (400 MHz, dimethyl sulfoxide-d6) δ ppm 7.37-7.30 (m, 4H), 7.29-7.24 (m, 1H) 3.91 (s, 2H), 3.56 (q, J=13.2, 2H), 3.19 (dt, J=5.4, 7.4, 1H), 2.71-2.61 (m, 2H), 2.50-2.41 (m, 2H), 2.36-2.28 (m, 2H), 2.05-1.95 (m, 2H), 1.65-1.55 (m, 1H), 1.43-1.33 (m, 1H).

Workup

  1. filtrationThe slurry was filtered
  2. washthe cake was rinsed with ethanol (10 mL)

Sources & evidence

ORD record
ord-eb6acfb801a84733bb0831d40bf79016
Source dataset
uspto-grants-2014_04
Patent number
US08691865B2

Reaction notes

Loading…