Tetrahydrofuran → HCID 86628546, compound

HRID 732679Notes

Reaction equation

HRID 732679 reaction equation
C1COCC1.[C:6]1([C@H:16]([N:18]([CH2:26][C@@H:27]2[C@@H:31]([C:32]3[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=3)[CH2:30][NH:29][CH2:28]2)[C:19](=[O:25])[O:20][C:21]([CH3:24])([CH3:23])[CH3:22])[CH3:17])[C:15]2[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=2)[CH:9]=[CH:8][CH:7]=1.[CH:38]1[N:42]=[CH:41][N:40]([C:43](N2C=NC=C2)=[O:44])[CH:39]=1>C(N(CC)CC)C>[N:40]1([C:43]([N:29]2[CH2:30][C@H:31]([C:32]3[CH:33]=[CH:34][CH:35]=[CH:36][CH:37]=3)[C@@H:27]([CH2:26][N:18]([C@@H:16]([C:6]3[C:15]4[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=4)[CH:9]=[CH:8][CH:7]=3)[CH3:17])[C:19](=[O:25])[O:20][C:21]([CH3:23])([CH3:24])[CH3:22])[CH2:28]2)=[O:44])[CH:39]=[CH:38][N:42]=[CH:41]1

Participants

5

Reactant 3

HCID 8028TetrahydrofuranHCID 682631,1'-CarbonyldiimidazoleHCID 86628525tert-butyl [(1R)-1-(1-naphthyl)ethyl]{[(3R,4S)-4-phenylpyrrolidin-3-yl]methyl}carbamate

Product 1

HCID 86628546HCID 86628546, compoundYield 107.4%

Reagents, catalysts & solvents 1

HCID 8471TriethylamineSolvent

Procedure

A 10 ml THF solution of 940 mg of tert-butyl [(1R)-1-(1-naphthyl)ethyl]{[(3R,4S)-4-phenylpyrrolidin-3-yl]methyl}carbamate was mixed with 0.3 ml of triethylamine and 3.54 g of CDI and stirred at room temperature for 2Hours. The reaction solution was concentrated under a reduced pressure and diluted with ethyl acetate. This was washed with 1 M hydrochloric acid and saturated brine, and the organic layer was dried with anhydrous magnesium sulfate. By evaporating the solvent under a reduced pressure, 1.23 g of tert-butyl {[(3R,4S)-1-(1H-imidazol-1-ylcarbonyl)-4-phenylpyrrolidin-3-yl]methyl}[(1R)-1-(1-naphthyl)ethyl]carbamate was obtained as a pale yellow amorphous substance. EP: 525.

Workup

  1. concentrationThe reaction solution was concentrated under a reduced pressure
  2. additiondiluted with ethyl acetate
  3. washThis was washed with 1 M hydrochloric acid and saturated brine
  4. dry with materialthe organic layer was dried with anhydrous magnesium sulfate
  5. customBy evaporating the solvent under a reduced pressure

Sources & evidence

ORD record
ord-6c16113ac3744bc3b9bb13b25e84882a
Source dataset
uspto-grants-2009_09
Patent number
US07585886B2

Reaction notes

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