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Sodium Thiosulfate → tert-butyl (1S,3S,5S)-3-formyl-2-azabicyclo[3.1.0]hexane-2-carboxylate

HRID 2064790
Notes
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Reaction equation

HRID 2064790 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:35]([CH2:36][OH:37])[CH2:34][C@H:33]2[C@@H:31]1[CH2:32]2)=[O:29])([CH3:26])([CH3:25])[CH3:24].C([O-])(O)=O.[Na+].[O-]S([O-])(=S)=O.[Na+].[Na+]>C(Cl)Cl>[C:23]([O:27][C:28]([N:30]1[C@H:35]([CH:36]=[O:37])[CH2:34][C@H:33]2[C@@H:31]1[CH2:32]2)=[O:29])([CH3:26])([CH3:25])[CH3:24]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 24477Sodium ThiosulfateHCID 159087TriacetoxyperiodinaneHCID 516892Sodium BicarbonateHCID 10899963tert-Butyl (1S,3S,5S)-3-(hydroxymethyl)-2-azabicyclo[3.1.0]hexane-2-carboxylate

Product 1

HCID 58278672tert-butyl (1S,3S,5S)-3-formyl-2-azabicyclo[3.1.0]hexane-2-carboxylate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Dess-Martin periodinane (39.4 mmol, 2.1 eq) is added to a solution of (1S,3S,5S)-3-hydroxymethyl-2-aza-bicyclo[3.1.0]hexane-2-carboxylic acid tert-butyl ester (18.8 mmol, 1.0 eq) in DCM (300 mL). After 2 h sat. NaHCO3 solution and aqueous Na2S2O3 solution are added, the layers are separated and the aqueous layer is extracted twice with DCM. The combined organic layers are washed twice with NaOH solution (1.0 M), water and brine, dried over Na2SO4 and concentrated in vacuo to give the desired product as an orange oil which is used without further purification.

Workup

  1. customthe layers are separated
  2. extractionthe aqueous layer is extracted twice with DCM
  3. washThe combined organic layers are washed twice with NaOH solution (1.0 M), water and brine
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-2bb99c62577546eb9d643c574ee6a0fe
Source dataset
uspto-grants-2012_10
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08288435B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes