HCID 86596877, compound → HCID 68769972, compound

HRID 1171550Notes

Reaction equation

HRID 1171550 reaction equation
[OH:1][CH:2]([C@@H:5]1[CH2:10][C@H:9]([N:11]([CH:13]([CH3:15])[CH3:14])[CH3:12])[CH2:8][CH2:7][C@@H:6]1[N:16]1[CH2:20][CH2:19][C@H:18]([NH:21]C(=O)OCC2C=CC=CC=2)[C:17]1=[O:32])[CH2:3][CH3:4]>CO.[Pd]>[NH2:21][C@H:18]1[CH2:19][CH2:20][N:16]([C@H:6]2[CH2:7][CH2:8][C@@H:9]([N:11]([CH:13]([CH3:14])[CH3:15])[CH3:12])[CH2:10][C@H:5]2[CH:2]([OH:1])[CH2:3][CH3:4])[C:17]1=[O:32]

Participants

4

Reactant 1

HCID 86596877HCID 86596877, compound

Product 1

HCID 68769972HCID 68769972, compoundYield 101.8%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A solution of benzyl (S)-1-((1S,2R,4R)-2-(1-hydroxypropyl)-4-(isopropyl(methyl)amino)cyclohexyl)-2-oxopyrrolidin-3-ylcarbamate (267 mg) in MeOH (15 mL) was charged with 10% Pd/C, Degussa (100 mg). The reaction flask was evacuated and then back-filled with hydrogen; this was repeated two more times. The reaction was stirred under 60 psi of H2 for 4 h and then filtered and concentrated in vacuo to afford the desired (S)-3-amino-1-((1S,2R,4R)-2-(1-hydroxypropyl)-4-(isopropyl(methyl)amino)cyclohexyl)pyrrolidin-2-one (190 mg) as an oil.

Workup

  1. customThe reaction flask was evacuated
  2. additionback-filled with hydrogen
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-03da87556a454a73bbe7b29fa3359934
Source dataset
uspto-grants-2010_11
Patent number
US07829571B2

Reaction notes

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