(6-{2-[Bis-(4-methoxy-phenyl)-phenyl-methoxymethyl]-4-hydroxy-pyrrolidin-1-yl}-6-oxo-hexyl)-carbamic Acid Benzyl Ester → 6-Amino-1-{2-[bis-(4-methoxy-phenyl)-phenyl-methoxymethyl]-4-hydroxy-pyrrolidin-1-yl}-hexan-1-one

HRID 20894Notes

Reaction equation

HRID 20894 reaction equation
C(OC(=O)[NH:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][C:16]([N:18]1[CH2:22][CH:21]([OH:23])[CH2:20][CH:19]1[CH:24]([C:43]1[CH:48]=[CH:47][CH:46]=[CH:45][CH:44]=1)[O:25][CH:26]([C:35]1[CH:40]=[CH:39][C:38]([O:41][CH3:42])=[CH:37][CH:36]=1)[C:27]1[CH:32]=[CH:31][C:30]([O:33][CH3:34])=[CH:29][CH:28]=1)=[O:17])C1C=CC=CC=1>C(OCC)(=O)C>[NH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][C:16]([N:18]1[CH2:22][CH:21]([OH:23])[CH2:20][CH:19]1[CH:24]([C:43]1[CH:48]=[CH:47][CH:46]=[CH:45][CH:44]=1)[O:25][CH:26]([C:35]1[CH:40]=[CH:39][C:38]([O:41][CH3:42])=[CH:37][CH:36]=1)[C:27]1[CH:32]=[CH:31][C:30]([O:33][CH3:34])=[CH:29][CH:28]=1)=[O:17]

Participants

3

Reactant 1

HCID 131728206(6-{2-[Bis-(4-methoxy-phenyl)-phenyl-methoxymethyl]-4-hydroxy-pyrrolidin-1-yl}-6-oxo-hexyl)-carbamic Acid Benzyl Ester

Product 1

HCID 1317282076-Amino-1-{2-[bis-(4-methoxy-phenyl)-phenyl-methoxymethyl]-4-hydroxy-pyrrolidin-1-yl}-hexan-1-oneYield 91.4%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

Compound 4a (14.5 g, 21.7 mmol) was dissolved in ethyl acetate (100 mL) and purged with argon. To the solution was added 10% palladium on carbon (2 g). The flask was purged with hydrogen 2 times and stirred further at room temperature under hydrogen atmosphere for overnight. The disappearance of the starting material was confirmed by the TLC. The reaction mixture was filtered through a pad of Celite and washed with ethyl acetate. The combined organic layer was concentrated under reduced pressure to afford compound 5 (10.56 g, 91%) as white solid. This was used as such for the next step.

Workup

  1. custompurged with argon
  2. additionTo the solution was added 10% palladium on carbon (2 g)
  3. customThe flask was purged with hydrogen 2 times
  4. filtrationThe reaction mixture was filtered through a pad of Celite
  5. washwashed with ethyl acetate
  6. concentrationThe combined organic layer was concentrated under reduced pressure

Sources & evidence

ORD record
ord-a58bde882d654e5c9f825f4ce9a5c1f8
Source dataset
uspto-grants-2010_06
Patent number
US07745608B2

Reaction notes

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