Acetic Acid → HCID 131733511, compound

HRID 2281004Notes

Reaction equation

HRID 2281004 reaction equation
CC(O)=O.C([N:12]1[CH2:16][C@@H:15]([C:17]2[CH:22]=[CH:21][CH:20]=[C:19]([O:23][C:24]([F:27])([F:26])[F:25])[CH:18]=2)[C@H:14]([NH:28][C:29](=[O:37])[O:30][CH2:31][CH2:32][Si:33]([CH3:36])([CH3:35])[CH3:34])[CH2:13]1)C1C=CC=CC=1.OCC1(OC[C@@H](O)[C@@H](O)[C@H]1O)O>CCO.[Pd]>[F:27][C:24]([F:25])([F:26])[O:23][C:19]1[CH:18]=[C:17]([C@@H:15]2[CH2:16][NH:12][CH2:13][C@H:14]2[NH:28][C:29](=[O:37])[O:30][CH2:31][CH2:32][Si:33]([CH3:34])([CH3:36])[CH3:35])[CH:22]=[CH:21][CH:20]=1

Participants

6

Reactant 3

HCID 176Acetic AcidHCID 441036D-PsicoseHCID 131733512HCID 131733512, compound

Product 1

HCID 131733511HCID 131733511, compoundYield 83.2%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

AcOH (2 mL) was added to a solution of 2-(trimethylsilyl)ethyl [trans-benzyl-4-(3-trifluoromethoxyphenyl)pyrrolidin-3-yl]carbamate (2.50 g; 6.03 mmol) in EtOH (150 ml). Pd/C (1.25 g, wet, 10% Pd) was then added, and the reaction mixture was put on a par shaker (60 Psi), and reacted for 2 h. The reaction mixture was filtered, and the filtrate was concentrated to provide the title compound (1.96 g, quantitative yield).

Workup

  1. customreacted for 2 h
  2. filtrationThe reaction mixture was filtered
  3. concentrationthe filtrate was concentrated

Sources & evidence

ORD record
ord-6139ef6081e9431e9dba85006c255cfa
Source dataset
uspto-grants-2015_09
Patent number
US09139568B2

Reaction notes

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