Sodium Sulfite → tert-Butyl hydrogen ((4-formylphenyl)methyl)carbonimidate

HRID 2277005Notes

Reaction equation

HRID 2277005 reaction equation
[C:1]([O:5][C:6](=[O:17])[NH:7][CH2:8][C:9]1[CH:14]=[CH:13][C:12]([CH2:15][OH:16])=[CH:11][CH:10]=1)([CH3:4])([CH3:3])[CH3:2].C(=O)=O.CC(C)=O.CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O.C(=O)(O)[O-].[Na+].S([O-])([O-])=O.[Na+].[Na+]>C(Cl)Cl>[C:1]([O:5][C:6](=[O:17])[NH:7][CH2:8][C:9]1[CH:10]=[CH:11][C:12]([CH:15]=[O:16])=[CH:13][CH:14]=1)([CH3:4])([CH3:2])[CH3:3]

Participants

7

Reactant 5

HCID 24437Sodium SulfiteHCID 159087TriacetoxyperiodinaneHCID 516892Sodium BicarbonateHCID 2794813tert-Butyl [4-(hydroxymethyl)benzyl]carbamateHCID 18522661Acetone cardice

Product 1

HCID 2794832tert-Butyl hydrogen ((4-formylphenyl)methyl)carbonimidateYield 287.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

(4-Hydroxymethyl-benzyl)-carbamic acid tert-butyl ester (480 mg, 0.71 mmol) was dissolved in DCM (3 mL) and cooled to −78° C. (dry ice/acetone). Dess-Martin periodinane (331 mg, 0.78 mmol) was added to the reaction which was allowed to warm to r.t and stir for 3 h. A 1:1 solution of saturated sodium bicarbonate and sodium sulfite (20 mL) was added and the reaction mixture stirred vigorously for 15 min. The organic layer was isolated, washed with saturated sodium bicarbonate (10 mL), dried (Na2SO4) and evaporated to dryness to afford the desired compound (480 mg, 100%). m/z 258 [M++Na]+

Workup

  1. temperatureto warm
  2. stirringthe reaction mixture stirred vigorously for 15 min
  3. customThe organic layer was isolated
  4. washwashed with saturated sodium bicarbonate (10 mL)
  5. dry with materialdried (Na2SO4)
  6. customevaporated to dryness

Sources & evidence

ORD record
ord-f362d04dac5b4d88845f671747cd42c3
Source dataset
uspto-grants-2015_09
Patent number
US09133104B2

Reaction notes

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