Potassium Carbonate → HCID 131734817, compound

HRID 1778500Notes

Reaction equation

HRID 1778500 reaction equation
C([O:4][CH2:5][CH:6]1[CH2:10][CH2:9][C:8]([CH2:20][O:21][Si:22]([C:25]([CH3:28])([CH3:27])[CH3:26])([CH3:24])[CH3:23])([CH2:11][O:12][Si:13]([C:16]([CH3:19])([CH3:18])[CH3:17])([CH3:15])[CH3:14])[NH:7]1)(=O)C.C([O-])([O-])=O.[K+].[K+]>CO>[Si:22]([O:21][CH2:20][C:8]1([CH2:11][O:12][Si:13]([C:16]([CH3:19])([CH3:18])[CH3:17])([CH3:14])[CH3:15])[NH:7][CH:6]([CH2:5][OH:4])[CH2:10][CH2:9]1)([C:25]([CH3:28])([CH3:27])[CH3:26])([CH3:24])[CH3:23]

Participants

4

Reactant 2

HCID 11430Potassium CarbonateHCID 131734815HCID 131734815, compound

Product 1

HCID 131734817HCID 131734817, compoundYield 98.7%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
25 °C

Procedure

A mixture of [5,5-bis[[tert-butyl(dimethyl)silyl]oxymethyl]pyrrolidin-2-yl]methyl acetate (4.48 g, 10.4 mmol) and K2CO3 (g, mmol) in methanol (50 mL) was stirred at 25° C. for 2 h. Then the insoluble solid was filtered off and the filtrate was concentrated in vacuo. And then the residue was extracted with ethyl acetate (50 mL) two times, washed with water (20 mL) three times, dried over anhydrous sodium sulfate and concentrated in vacuo to afford [5,5-bis[[tert-butyl(dimethyl)silyl]oxymethyl]pyrrolidin-2-yl]methanol 81g (4 g, 98%) which was used for next step without further purification. MS: calc'd (MH+) 390, measured (MH+) 390.

Workup

  1. filtrationThen the insoluble solid was filtered off
  2. concentrationthe filtrate was concentrated in vacuo
  3. extractionAnd then the residue was extracted with ethyl acetate (50 mL) two times
  4. washwashed with water (20 mL) three times
  5. dry with materialdried over anhydrous sodium sulfate
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-5128aca300a14b85a786973eacb2681b
Source dataset
uspto-grants-2016_02
Patent number
US09266904B2

Reaction notes

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