Pyrrolidin-2-ylmethyl-carbamic acid tert-butyl ester → tert-Butyl ({1-[(2R)-2-hydroxy-2-(4-methyl-1-oxo-1,3-dihydro-2-benzofuran-5-yl)ethyl]pyrrolidin-2-yl}methyl)carbamate

HRID 515112Notes

Reaction equation

HRID 515112 reaction equation
[CH3:1][C:2]1[C:10]2[CH2:9][O:8][C:7](=[O:11])[C:6]=2[CH:5]=[CH:4][C:3]=1[C@@H:12]1[CH2:14][O:13]1.[C:15]([O:19][C:20](=[O:28])[NH:21][CH2:22][CH:23]1[CH2:27][CH2:26][CH2:25][NH:24]1)([CH3:18])([CH3:17])[CH3:16]>C(O)C>[C:15]([O:19][C:20](=[O:28])[NH:21][CH2:22][CH:23]1[CH2:27][CH2:26][CH2:25][N:24]1[CH2:14][C@H:12]([OH:13])[C:3]1[CH:4]=[CH:5][C:6]2[C:7](=[O:11])[O:8][CH2:9][C:10]=2[C:2]=1[CH3:1])([CH3:18])([CH3:16])[CH3:17]

Participants

4

Reactant 2

HCID 21834643Pyrrolidin-2-ylmethyl-carbamic acid tert-butyl esterHCID 595686464-Methyl-5-((2R)-oxiran-2-yl)-2-benzofuran-1(3H)-one

Product 1

HCID 131733295tert-Butyl ({1-[(2R)-2-hydroxy-2-(4-methyl-1-oxo-1,3-dihydro-2-benzofuran-5-yl)ethyl]pyrrolidin-2-yl}methyl)carbamate

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Six vials containing a solution of 4-methyl-5-[(2R)-oxiran-2-yl]-2-benzofuran-1(3H)-one (325 mg, 1.67 mmol) in 12 mL ethanol added to tert-butyl(pyrrolidin-2-ylmethyl)carbamate (333 mg, 1.67 mmol) were prepared. The reaction mixtures were microwaved at 140° C. for 55 minutes. The solutions were combined and the solvents were removed in vacuo. The resulting residue was purified by HPLC to afford two diastereomers of tert-butyl({1-[(2R)-2-hydroxy-2-(4-methyl-1-oxo-1,3-dihydro-2-benzofuran-5-yl)ethyl]pyrrolidin-2-yl}methyl)carbamate:

Workup

  1. customwere prepared
  2. customThe reaction mixtures
  3. customwere microwaved at 140° C. for 55 minutes
  4. customthe solvents were removed in vacuo
  5. customThe resulting residue was purified by HPLC

Sources & evidence

ORD record
ord-24f624a4da4645c7aab5fe575b75b6c9
Source dataset
uspto-grants-2015_08
Patent number
US09108947B2

Reaction notes

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