4-Methylmorpholine → (2S)-1-[N-(tert-Butoxycarbonyl)-L-prolyl]-2-[1-hydroxy-2(4-methoxyphenoxy)ethyl]pyrrolidine

HRID 1720532Notes

Reaction equation

HRID 1720532 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.[C:25]([O:29][C:30]([N:32]1[CH2:39][CH2:38][CH2:37][C@H:33]1C(O)=O)=[O:31])([CH3:28])([CH3:27])[CH3:26].CN1CCOCC1.C1C=CC2N(O)N=NC=2C=1.C1CCC(N=C=NC2CCCCC2)CC1>Cl.O1CCOCC1>[C:25]([O:29][C:30]([N:32]1[CH2:39][CH2:38][CH2:37][C@H:33]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:31])([CH3:28])([CH3:26])[CH3:27]

Participants

7

Reactant 5

HCID 79724-MethylmorpholineHCID 10868DicyclohexylcarbodiimideHCID 757711-HydroxybenzotriazoleHCID 850831,2-Pyrrolidinedicarboxylic acid, 1-(1,1-dimethylethyl) ester, (2S)-HCID 57133844(S)-1-(tert-Butoxycarbonyl)-2-[1-hydroxy-2-(p-methoxyphenoxy)ethyl]pyrrolidine

Product 1

HCID 22860058(2S)-1-[N-(tert-Butoxycarbonyl)-L-prolyl]-2-[1-hydroxy-2(4-methoxyphenoxy)ethyl]pyrrolidineYield 69.8%

Reagents, catalysts & solvents 1

HCID 204431481,4-Dioxane hydrochlorideSolvent

Procedure

(2S)-1-(tert-Butoxycarbonyl)-2-[1-hydroxy-2-(4-methoxyphenoxy)ethyl]pyrrolidine (1.57 g) was dissolved in 4N hydrochloric acid/1,4-dioxane (23 ml), and the mixture was stirred at room temperature for 1 hour. The residue obtained by concentration and drying of the reaction mixture was dissolved in DMF (15 ml), and subjected to the condensation reaction using N-(tert-butoxycarbonyl)-L-proline (1.00 g), N-methylmorpholine (0.51 ml), HOBt (0.75 g) and DCC (0.96 g) in the same manner as in Example 46-C) to give 1.41 g of the title compound.

Workup

  1. customThe residue obtained by concentration
  2. customdrying of the reaction mixture
  3. dissolutionwas dissolved in DMF (15 ml)
  4. customsubjected to the condensation reaction

Sources & evidence

ORD record
ord-0e3d9cd70a134f2a88951f925dc56bff
Source dataset
uspto-grants-1996_04
Patent number
US05506256

Reaction notes

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