Triacetoxyperiodinane → 4-Boc-1-Cbz-piperazine-2-carbaldehyde

HRID 2371186Notes

Reaction equation

HRID 2371186 reaction equation
[OH:1][CH2:2][CH:3]1[CH2:8][N:7]([C:9]([O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:10])[CH2:6][CH2:5][N:4]1[C:16]([O:18][CH2:19][C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)=[O:17].CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O>C(Cl)Cl>[CH:2]([CH:3]1[CH2:8][N:7]([C:9]([O:11][C:12]([CH3:15])([CH3:13])[CH3:14])=[O:10])[CH2:6][CH2:5][N:4]1[C:16]([O:18][CH2:19][C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)=[O:17])=[O:1]

Participants

4

Reactant 2

HCID 159087TriacetoxyperiodinaneHCID 235310394-(1,1-Dimethylethyl) 1-(phenylmethyl) 2-(hydroxymethyl)-1,4-piperazinedicarboxylate

Product 1

HCID 596715274-Boc-1-Cbz-piperazine-2-carbaldehydeYield 57.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To 1-benzyl 4-tert-butyl 2-(hydroxymethyl)piperazine-1,4-dicarboxylate (0.4 g) in CH2Cl2 (10 ml) under argon was added Dess Martin periodinane (533 mg), the mixture stirred at room temperature for 16 hours, evaporated to half volume, saturated aqueous sodium bicarbonate and ethyl acetate added, the organic phase dried (MgSO4), and evaporated to give the title compound (228 mg, 57%).

Workup

  1. customevaporated to half volume, saturated aqueous sodium bicarbonate and ethyl acetate
  2. additionadded
  3. dry with materialthe organic phase dried (MgSO4)
  4. customevaporated

Sources & evidence

ORD record
ord-1520dff97d0d4c9081ea84cd59d19608
Source dataset
uspto-grants-2014_04
Patent number
US08710224B2

Reaction notes

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