Water → HCID 58104590, compound

HRID 2064481Notes

Reaction equation

HRID 2064481 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[C@H:37]([CH2:38][OH:39])[CH2:36][C@H:35]2[C@@H:31]1[CH2:32][CH2:33][CH2:34]2)=[O:29])([CH3:26])([CH3:25])[CH3:24].O.[OH-].[Na+]>C(Cl)Cl.CCOCC>[C:23]([O:27][C:28]([N:30]1[C@H:37]([CH:38]=[O:39])[CH2:36][C@H:35]2[C@@H:31]1[CH2:32][CH2:33][CH2:34]2)=[O:29])([CH3:26])([CH3:25])[CH3:24]

Participants

7

Reactant 4

HCID 962WaterHCID 14798Sodium HydroxideHCID 159087TriacetoxyperiodinaneHCID 66845455HCID 66845455, compound

Product 1

HCID 58104590HCID 58104590, compound

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 6344DichloromethaneSolvent2×

Procedure

A solution of Dess-Martin periodinane (4.14 mmol, 2.2 eq) in DCM (10 ml) is treated with a solution of (1S,3S,5S)-3-hydroxymethyl-2-azabicyclo[3.3.0]octane-2-carboxylic acid tert-butyl ester (1.85 mmol, 1.0 eq) in DCM (4 mL) and some drops of water. After 5 h ether and aqueous NaOH solution (1.0 M) are added and the layers are separated. The organic layer is washed with aqueous citric acid (10%) and brine, dried over MgSO4 and concentrated in vacuo to give the desired aldehyde which is used without further purification.

Workup

  1. customthe layers are separated
  2. washThe organic layer is washed with aqueous citric acid (10%) and brine
  3. dry with materialdried over MgSO4
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-8001284c172c4747a319173a0ce5df26
Source dataset
uspto-grants-2012_10
Patent number
US08288429B2

Reaction notes

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