Water → HCID 86592434, compound

HRID 273190Notes

Reaction equation

HRID 273190 reaction equation
C([O:4][C:5]1[CH:33]=[CH:32][C:8]([CH2:9][N:10]2[CH2:14][CH:13]([CH2:15][CH2:16][CH2:17][CH3:18])[CH:12]([CH2:19][N:20]([O:23][CH2:24][C:25]3[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=3)[CH:21]=[O:22])[C:11]2=[O:31])=[CH:7][CH:6]=1)C=C.N1CCOCC1.O>ClCCl.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[CH2:24]([O:23][N:20]([CH2:19][CH:12]1[CH:13]([CH2:15][CH2:16][CH2:17][CH3:18])[CH2:14][N:10]([CH2:9][C:8]2[CH:32]=[CH:33][C:5]([OH:4])=[CH:6][CH:7]=2)[C:11]1=[O:31])[CH:21]=[O:22])[C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1

Participants

6

Reactant 3

HCID 962WaterHCID 8083MorpholineHCID 86592432HCID 86592432, compound

Product 1

HCID 86592434HCID 86592434, compoundYield 88.7%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 6344DichloromethaneSolvent

Procedure

To a solution of (+/−)-(3RS,4SR)-N-[1-(4-allyloxybenzyl)-4-butyl-2-oxopyrrolidin-3-yl-methyl]-N-benzyloxyformamide (2.6 g, 5.77 mmol) in dichloromethane (60 mL) under argon was added morpholine (6 mL), water (1.2 mL) and then tetrakis(triphenylphosphine)palladium (0.33 g, 0.28 mmol). The reaction mixture was stirred at rt for 1 h, filtered through a Celite pad and concentrated. The residue was purified by flash column chromatography (silica gel, ethyl acetate/hexanes 4:1) to afford (+/−)-(3RS,4SR)-N-benzyloxy-N-[4-butyl-1-(4-hydroxybenzyl)-2-oxopyrrolidin-3-yl-methyl]formamide as a white solid (2.1 g, 88%). MS(ES) m/e 411 [M+H]+.

Workup

  1. filtrationfiltered through a Celite pad
  2. concentrationconcentrated
  3. customThe residue was purified by flash column chromatography (silica gel, ethyl acetate/hexanes 4:1)

Sources & evidence

ORD record
ord-7c01cfba09034eb387ad3903cefffd0c
Source dataset
uspto-grants-2008_11
Patent number
US07456211B2

Reaction notes

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