Triacetoxyperiodinane → 946484-82-8

HRID 1644800Notes

Reaction equation

HRID 1644800 reaction equation
CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O.[C:23]([O:27][C:28]([N:30]1[CH2:34][CH2:33][CH2:32][C:31]1([CH2:36][OH:37])[CH3:35])=[O:29])([CH3:26])([CH3:25])[CH3:24]>C(Cl)Cl>[C:23]([O:27][C:28]([N:30]1[CH2:34][CH2:33][CH2:32][C:31]1([CH:36]=[O:37])[CH3:35])=[O:29])([CH3:26])([CH3:25])[CH3:24]

Participants

4

Reactant 2

HCID 159087TriacetoxyperiodinaneHCID 23512318Tert-butyl 2-(hydroxymethyl)-2-methylpyrrolidine-1-carboxylate

Product 1

HCID 22456683946484-82-8Yield 84%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Dess Martin Periodinane (7.8 g, 0.0186 mol) was added in one portion to the solution of (rac)-2-hydroxymethyl-2-methyl-pyrrolidine-1-carboxylic acid tert-butyl ester (2 g, 0.0093 mol) in DCM (50 mL) under an inert atmosphere. The reaction was stirred until completion (about 2 h) then quenched with saturated solution of sodium thiosulphate, extracted with DCM (3×100 mL) washed with brine (50 mL), dried over anhydrous sodium sulphate, and concentrated using a rotary evaporator to afford 1.6 g (84%) of (rac)-2-formyl-2-methyl-pyrrolidine-1-carboxylic acid tert-butyl ester as a light brown colored oil.

Workup

  1. customthen quenched with saturated solution of sodium thiosulphate
  2. extractionextracted with DCM (3×100 mL)
  3. washwashed with brine (50 mL)
  4. dry with materialdried over anhydrous sodium sulphate
  5. concentrationconcentrated
  6. customa rotary evaporator

Sources & evidence

ORD record
ord-29526560096148359db32adf3dffadf2
Source dataset
uspto-grants-2012_02
Patent number
US08124636B2

Reaction notes

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