Water → HCID 86628130, compound

HRID 2354094Notes

Reaction equation

HRID 2354094 reaction equation
[NH:1]1[CH2:5][CH2:4][C@@H:3]([NH:6][C:7](=[O:13])[O:8][C:9]([CH3:12])([CH3:11])[CH3:10])[CH2:2]1.I[CH2:15][C:16]12[O:22][CH:19]([CH2:20][CH2:21]1)[CH2:18][CH2:17]2.C([O-])([O-])=O.[K+].[K+].O>CN(C=O)C>[C:16]12([CH2:15][N:1]3[CH2:5][CH2:4][C@@H:3]([NH:6][C:7](=[O:13])[O:8][C:9]([CH3:10])([CH3:12])[CH3:11])[CH2:2]3)[O:22][CH:19]([CH2:20][CH2:21]1)[CH2:18][CH2:17]2

Participants

6

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 1514397(3R)-(+)-3-(tert-Butoxycarbonylamino)pyrrolidineHCID 67035019HCID 67035019, compound

Product 1

HCID 86628130HCID 86628130, compoundYield 52.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
75 °C

Procedure

The mixture of tert-butyl (3R)-3-pyrrolidinylcarbamate (500 mg), 1-(iodomethyl)-7-oxabicyclo[2.2.1]heptane (639 mg) and K2CO3 (742 mg) in DMF (5 mL) was stirred at 75° C. for 32 hours. The resultant was added H2O, extracted with AcOEt. The organic phase was washed with brine, dried over Na2SO4, filtered, and evaporated in vacuo. The residue was purified by column chromatography on silica gel to give tert-butyl [(3R)-1-(7-oxabicyclo[2.2.1]hept-1-ylmethyl)-3-pyrrolidinyl]carbamate (416 mg) as orange oil.

Workup

  1. extractionextracted with AcOEt
  2. washThe organic phase was washed with brine
  3. dry with materialdried over Na2SO4
  4. filtrationfiltered
  5. customevaporated in vacuo
  6. customThe residue was purified by column chromatography on silica gel

Sources & evidence

ORD record
ord-22348c58282b464f8686b6ef8d6cd022
Source dataset
uspto-grants-2010_07
Patent number
US07750155B2

Reaction notes

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