Benzyloxycarbonyl-L-proline → (2S)-1-(N-Benzyloxycarbonyl-L-prolyl)-2-[l-hydroxy-2-(4-methoxyphenoxy)ethyl]pyrrolidine

HRID 1720493Notes

Reaction equation

HRID 1720493 reaction equation
C(O[C:6]([N:8]1[CH2:12][CH2:11][CH2:10][C@H:9]1[CH:13]([OH:24])[CH2:14][O:15][C:16]1[CH:21]=[CH:20][C:19]([O:22][CH3:23])=[CH:18][CH:17]=1)=[O:7])(C)(C)C.[CH2:25]([O:32][C:33]([N:35]1[CH2:42][CH2:41][CH2:40][C@H:36]1C(O)=O)=[O:34])[C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1>Cl.O1CCOCC1>[CH2:25]([O:32][C:33]([N:35]1[CH2:42][CH2:41][CH2:40][C@H:36]1[C:6]([N:8]1[CH2:12][CH2:11][CH2:10][C@H:9]1[CH:13]([OH:24])[CH2:14][O:15][C:16]1[CH:17]=[CH:18][C:19]([O:22][CH3:23])=[CH:20][CH:21]=1)=[O:7])=[O:34])[C:26]1[CH:27]=[CH:28][CH:29]=[CH:30][CH:31]=1

Participants

4

Reactant 2

HCID 101987Benzyloxycarbonyl-L-prolineHCID 57133844(S)-1-(tert-Butoxycarbonyl)-2-[1-hydroxy-2-(p-methoxyphenoxy)ethyl]pyrrolidine

Product 1

HCID 57161012(2S)-1-(N-Benzyloxycarbonyl-L-prolyl)-2-[l-hydroxy-2-(4-methoxyphenoxy)ethyl]pyrrolidineYield 57%

Reagents, catalysts & solvents 1

HCID 204431481,4-Dioxane hydrochlorideSolvent

Procedure

To (2S)-1-[t-butoxycarbonyl)-2-[1-hydroxy-2-(4-methoxyphenoxy)ethyl]pyrrolidine (14.03 g) was added 4N hydrochloric acid/1,4-dioxane (220 ml), and the mixture was stirred at room temperature for 1 hour. The reaction mixture was concentrated to dryness, and the residue was dissolved in DMF (100 ml), followed by condensation reaction as in Example 1-C) w i t h known N-benzyloxycarbonyl-L-proline (10.70 g) to give 11.10 g of the title compound.

Workup

  1. concentrationThe reaction mixture was concentrated to dryness
  2. dissolutionthe residue was dissolved in DMF (100 ml)
  3. customfollowed by condensation reaction as in Example 1-C) w i t h

Sources & evidence

ORD record
ord-3be758515d614d6f99fd2672f6ed0ab7
Source dataset
uspto-grants-1996_04
Patent number
US05506256

Reaction notes

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