(6-{2-[Bis-(4-methoxy-phenyl)-phenyl-methoxymethyl]-4-hydroxy-pyrrolidin-1-yl}-hexyl)-carbamic Acid Benzyl Ester → 1-(6-Amino-hexyl)-5-[bis-(4-methoxy-phenyl)-phenyl-methoxymethyl]-pyrrolidin-3-ol

HRID 2403002Notes

Reaction equation

HRID 2403002 reaction equation
C(OC(=O)[NH:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][N:17]1[CH2:21][CH:20]([OH:22])[CH2:19][CH:18]1[CH:23]([C:42]1[CH:47]=[CH:46][CH:45]=[CH:44][CH:43]=1)[O:24][CH:25]([C:34]1[CH:39]=[CH:38][C:37]([O:40][CH3:41])=[CH:36][CH:35]=1)[C:26]1[CH:31]=[CH:30][C:29]([O:32][CH3:33])=[CH:28][CH:27]=1)C1C=CC=CC=1>C(OCC)(=O)C>[NH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][N:17]1[CH:18]([CH:23]([C:42]2[CH:43]=[CH:44][CH:45]=[CH:46][CH:47]=2)[O:24][CH:25]([C:26]2[CH:31]=[CH:30][C:29]([O:32][CH3:33])=[CH:28][CH:27]=2)[C:34]2[CH:39]=[CH:38][C:37]([O:40][CH3:41])=[CH:36][CH:35]=2)[CH2:19][CH:20]([OH:22])[CH2:21]1

Participants

3

Reactant 1

HCID 131728214(6-{2-[Bis-(4-methoxy-phenyl)-phenyl-methoxymethyl]-4-hydroxy-pyrrolidin-1-yl}-hexyl)-carbamic Acid Benzyl Ester

Product 1

HCID 1317282151-(6-Amino-hexyl)-5-[bis-(4-methoxy-phenyl)-phenyl-methoxymethyl]-pyrrolidin-3-olYield 93%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

Compound 30 (6.52 g, 10 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 31 (4.8 g, 93%) 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-78706beea7424e918ca458150cf441e0
Source dataset
uspto-grants-2014_08
Patent number
US08796436B2

Reaction notes

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