Triacetoxyperiodinane → (1S,2S,5R)-2-Formyl-3-aza-bicyclo[3.1.0]hexane-3-carboxylic Acid Tert-butyl Ester

HRID 560336Notes

Reaction equation

HRID 560336 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[CH2:35][C@H:34]2[C@H:32]([CH2:33]2)[C@H:31]1[CH2:36][OH:37])=[O:29])([CH3:26])([CH3:25])[CH3:24].C([O-])(O)=O.[Na+]>C(Cl)Cl>[C:23]([O:27][C:28]([N:30]1[CH2:35][C@H:34]2[C@H:32]([CH2:33]2)[C@H:31]1[CH:36]=[O:37])=[O:29])([CH3:26])([CH3:25])[CH3:24]

Participants

5

Reactant 3

HCID 159087TriacetoxyperiodinaneHCID 516892Sodium BicarbonateHCID 39872284tert-butyl (1S,2S,5R)-2-(hydroxymethyl)-3-azabicyclo[3.1.0]hexane-3-carboxylate

Product 1

HCID 59444332(1S,2S,5R)-2-Formyl-3-aza-bicyclo[3.1.0]hexane-3-carboxylic Acid Tert-butyl Ester

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Dess-Martin periodinane (3.18 mmol) is added to a solution of (1S,2S,5R)-2-Hydroxymethyl-3-aza-bicyclo[3.1.0]hexane-3-carboxylic acid tert-butyl ester (3.24 mmol) in DCM (45 mL, saturated with water). Additional periodinane (0.80 mmol) is added after 2 h. After additional 2.5 h a sat. NaHCO3 solution is added, the layers are separated and the organic layer is washed with aq. Na2S2O3 solution. The aq. layer is extracted twice with DCM, the combined organic layers are concentrated in vacuo and the residue is purified by FC (pentane to pentane/ether 4/1) to give the desired product.

Workup

  1. additionAdditional periodinane (0.80 mmol) is added after 2 h
  2. customthe layers are separated
  3. washthe organic layer is washed with aq. Na2S2O3 solution
  4. extractionThe aq. layer is extracted twice with DCM
  5. concentrationthe combined organic layers are concentrated in vacuo
  6. customthe residue is purified by FC (pentane to pentane/ether 4/1)

Sources & evidence

ORD record
ord-c0a2712c07f7405396f6524cb6062e29
Source dataset
uspto-grants-2011_11
Patent number
US08063099B2

Reaction notes

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