HCID 68767765, compound → HCID 68769776, compound

HRID 1171515Notes

Reaction equation

HRID 1171515 reaction equation
C(OC(=O)[NH:10][C@H:11]1[CH2:15][CH2:14][N:13]([C@H:16]2[CH2:21][CH2:20][C@@H:19]([NH:22][C:23]([O:25][C:26]([CH3:29])([CH3:28])[CH3:27])=[O:24])[CH2:18][C@H:17]2[CH2:30][CH2:31][CH3:32])[C:12]1=[O:33])C1C=CC=CC=1>CO.[Pd]>[C:26]([O:25][C:23](=[O:24])[NH:22][C@@H:19]1[CH2:20][CH2:21][C@H:16]([N:13]2[CH2:14][CH2:15][C@H:11]([NH2:10])[C:12]2=[O:33])[C@H:17]([CH2:30][CH2:31][CH3:32])[CH2:18]1)([CH3:29])([CH3:28])[CH3:27]

Participants

4

Reactant 1

HCID 68767765HCID 68767765, compound

Product 1

HCID 68769776HCID 68769776, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A solution of {(3S)-1-[(1S,2R,4R)-4-tert-butoxycarbonylamino-2-propyl-cyclohexyl]-2-oxo-pyrrolidin-3-yl}-carbamic acid benzyl ester (185 mg, 0.54 mmol) in MeOH (8 mL) was charged with 5% Pd/C, Degussa (180 mg). The reaction flask was evacuated and then back-filled with hydrogen; this was repeated three more times. The reaction was stirred under 1 atm of H2 for 12 h and then filtered and concentrated in vacuo to afford (1R,3R,4S)-{4-[(3S)-3-amino-2-oxo-pyrrolidin-1-yl]-3-propyl-cyclohexyl}-carbamic acid tert-butyl ester. MS found: (M+H)+=340.3.

Workup

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

Sources & evidence

ORD record
ord-12677b5de599405eaffa1fa13cc4882a
Source dataset
uspto-grants-2010_11
Patent number
US07829571B2

Reaction notes

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