HCID 67705713, compound → HCID 54141268, compound

HRID 975679Notes

Reaction equation

HRID 975679 reaction equation
[CH2:1]([N:8]1[CH2:12][C@H:11]([O:13][Si:14]([C:17]([CH3:20])([CH3:19])[CH3:18])([CH3:16])[CH3:15])[CH2:10][C@H:9]1[CH:21]([C:23]1[N:27]([CH3:28])[C:26](C2SC=CC=2)=[N:25][CH:24]=1)[OH:22])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1>C(O)C.[Ni]>[CH2:1]([N:8]1[CH2:12][C@H:11]([O:13][Si:14]([C:17]([CH3:20])([CH3:19])[CH3:18])([CH3:16])[CH3:15])[CH2:10][C@H:9]1[CH:21]([C:23]1[N:27]([CH3:28])[CH:26]=[N:25][CH:24]=1)[OH:22])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 1

HCID 67705713HCID 67705713, compound

Product 1

HCID 54141268HCID 54141268, compoundYield 72.4%

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 702EthanolSolvent

Procedure

To a Raney-Nickel (NDT-90, 1400 ml) was added 1-{(2S,4R)-1-benzyl-4-(t-butyldimethylsilyloxy) pyrrolidin-2-yl}-1-(1-methyl-2-thiophenylimidazol-5-yl)methanol (222 g) in ethanol (4.4 l) under an atmosphere of nitrogen. The mixture was stirred and heated under reflux for 2.5 hours. After cooling, the Raney-Nickel was removed by filtration and washed with ethanol (1 l×5). The filtrate and the washings were combined, dried over magnesium sulfate, evaporated in vacuo to give 1-{(2S,4R)-1-benzyl-4-(t-butyldimethylsilyloxy) pyrrolidin-2-yl}-1-(1-methylimidazol-5-yl)methanol (133.4 g) as an amorphous solid.

Workup

  1. temperatureheated
  2. temperatureunder reflux for 2.5 hours
  3. temperatureAfter cooling
  4. customthe Raney-Nickel was removed by filtration
  5. washwashed with ethanol (1 l×5)
  6. dry with materialdried over magnesium sulfate
  7. customevaporated in vacuo

Sources & evidence

ORD record
ord-5fe1327d2d7d4fb7be0adf483c485196
Source dataset
uspto-grants-1997_03
Patent number
US05608056

Reaction notes

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