HCID 178418361, compound → HCID 178455534, compound

HRID 2279558Notes

Reaction equation

HRID 2279558 reaction equation
[CH3:1][C:2]([CH3:48])([CH3:47])[Si:3]([C:41]1[CH:46]=[CH:45][CH:44]=[CH:43][CH:42]=1)([C:35]1[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=1)[O:4][CH2:5][CH:6]([C:31]([F:34])([F:33])[F:32])[NH:7]/[C:8](=[N:20]/C(=O)OCC1C=CC=CC=1)/[NH:9]C(=O)OCC1C=CC=CC=1.[H][H]>CCO.C1COCC1.[OH-].[OH-].[Pd+2]>[Si:3]([O:4][CH2:5][CH:6]([NH:7][C:8]([NH2:20])=[NH:9])[C:31]([F:34])([F:33])[F:32])([C:2]([CH3:1])([CH3:47])[CH3:48])([C:41]1[CH:46]=[CH:45][CH:44]=[CH:43][CH:42]=1)[C:35]1[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=1

Participants

5

Reactant 2

HCID 178418361HCID 178418361, compound2×HCID 178455533HCID 178455533, compound

Product 1

HCID 178455534HCID 178455534, compoundYield 100%

Reagents, catalysts & solvents 2

HCID 9942167Palladium hydroxideCatalystHCID 21873804Tetrahydrofuran ethanolSolvent

Procedure

To a stirred solution of 346 (210 mg, 0.310 mmol) in 95% EtOH/THF (5 mL, 1:1) was added Pearlman's Catalyst (21.8 mg, 0.0310 mmol). The suspension was put through a vacuum/purge cycle three times with hydrogen gas and then maintained under 1 atmosphere of hydrogen pressure overnight. The mixture was then filtered through GF/F filter paper with 95% ethanol and the filtrate was concentrated to afford 127 mg (100%) of 1-(3-(tert-butyldiphenylsilyloxy)-1,1,1-trifluoropropan-2-yl)guanidine (348) as a white solid.

Workup

  1. filtrationThe mixture was then filtered through GF/F
  2. filtrationfilter paper with 95% ethanol
  3. concentrationthe filtrate was concentrated

Sources & evidence

ORD record
ord-946a9f08c2cb42ca98ae5bfd3950acc9
Source dataset
uspto-grants-2015_09
Patent number
US09133187B2

Reaction notes

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