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

HRID 603229Notes

Reaction equation

HRID 603229 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-f8dd782cb2bd4339bfb77978d6a413b0
Source dataset
uspto-grants-2011_03
Patent number
US07906645B2

Reaction notes

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