Trifluoroacetic acid → HCID 71293825, compound

HRID 446022Notes

Reaction equation

HRID 446022 reaction equation
C([O:5][C:6](=[O:39])[CH2:7][C@@:8]1([C:23]([NH:25][CH:26]2[CH2:31][CH2:30][N:29]([C:32](OC(C)(C)C)=O)[CH2:28][CH2:27]2)=[O:24])[C@H:12]([CH3:13])[CH2:11][N:10]([CH2:14][C:15]2[C:20]([CH3:21])=[CH:19][CH:18]=[CH:17][C:16]=2[Cl:22])[CH2:9]1)(C)(C)C.FC(F)(F)C(O)=O.[C:47]1(C=O)[CH2:51][CH2:50][CH2:49][CH:48]=1.C(N(CC)CC)C.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>O1CCCC1.ClCCl>[Cl:22][C:16]1[CH:17]=[CH:18][CH:19]=[C:20]([CH3:21])[C:15]=1[CH2:14][N:10]1[CH2:11][C@@H:12]([CH3:13])[C@@:8]([CH2:7][C:6]([OH:5])=[O:39])([C:23](=[O:24])[NH:25][CH:26]2[CH2:27][CH2:28][N:29]([CH2:32][C:47]3[CH2:51][CH2:50][CH2:49][CH:48]=3)[CH2:30][CH2:31]2)[CH2:9]1

Participants

8

Reactant 5

HCID 6422Trifluoroacetic acidHCID 8471TriethylamineHCID 1386721-Cyclopentene-1-carboxaldehydeHCID 5049666Sodium triacetoxyborohydrideHCID 71293807HCID 71293807, compound

Product 1

HCID 71293825HCID 71293825, compoundYield 42.9%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolvent

Procedure

A mixture of tert-butyl 4-[(3R*,4S*)-3-[(2-tert-butoxy)-2-oxoethyl]-1-[(2-chloro-6-methylphenyl)methyl]-4-methylpyrrolidin-3-amido}piperidine-1-carboxylate obtained in Example 8a (237 mg, 0.42 mmol), trifluoroacetic acid (2.3 ml, 31 mmol) and dichloromethane (dehydrated) (2.3 ml) was stirred at mom temperature for three hours and 30 minutes. The reaction mixture was concentrated, and cyclopent-1-ene-1-carbaldehyde obtained in Example 7a (121 mg, 1.26 mmol), triethylamine (0.176 ml, 1.26 mmol) and tetrahydrofuran (5 ml) were added to the resulting residue, followed by stirring for 35 minutes. Sodium triacetoxyborohydride (267 mg, 1.26 mmol) was added to the reaction mixture, which was stirred at room temperature for 13 hours. The reaction mixture was concentrated, and the resulting residue was purified by silica gel column chromatography (ODS silica gel, elution solvent: water/methanol) twice to give the title compound (88 mg, yield 42.9%).

Workup

  1. concentrationThe reaction mixture was concentrated
  2. stirringby stirring for 35 minutes
  3. stirringwas stirred at room temperature for 13 hours
  4. concentrationThe reaction mixture was concentrated
  5. customthe resulting residue was purified by silica gel column chromatography (ODS silica gel, elution solvent: water/methanol) twice

Sources & evidence

ORD record
ord-e1aa37f88bc94c8fb8dc54aa55faedc4
Source dataset
uspto-grants-2013_07
Patent number
US08476301B2

Reaction notes

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