Triacetoxyperiodinane → (1R)-4'-(4-Chlorophenyl)-2',3',9'-trimethylspiro[cyclopropane-1,6'-thieno[3,2-f][1,2,4]triazolo[4,3-a][1,4]diazepine]-2-carbaldehyde

HRID 1772344Notes

Reaction equation

HRID 1772344 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:14]3[C:15]([CH3:19])=[C:16]([CH3:18])[S:17][C:13]=3[N:12]3[C:20]([CH3:23])=[N:21][N:22]=[C:11]3[C@@:10]3([CH2:25][C@H:24]3[CH2:26][OH:27])[N:9]=2)=[CH:4][CH:3]=1.CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O>C(Cl)Cl.C(OCC)C>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[C:14]3[C:15]([CH3:19])=[C:16]([CH3:18])[S:17][C:13]=3[N:12]3[C:20]([CH3:23])=[N:21][N:22]=[C:11]3[C@:10]3([CH2:25][CH:24]3[CH:26]=[O:27])[N:9]=2)=[CH:6][CH:7]=1

Participants

5

Reactant 2

HCID 159087Triacetoxyperiodinane2×HCID 57404763((1S,2R)-4'-(4-chlorophenyl)-2',3',9'-trimethylspiro[cyclopropane-1,6'-thieno[3,2-f][1,2,4]triazolo[4,3-a][1,4]diazepin]-2-yl)methanol2×

Product 1

HCID 86706922(1R)-4'-(4-Chlorophenyl)-2',3',9'-trimethylspiro[cyclopropane-1,6'-thieno[3,2-f][1,2,4]triazolo[4,3-a][1,4]diazepine]-2-carbaldehyde

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 6344DichloromethaneSolvent

Procedure

To a solution of ((1S,2R)-4′-(4-chlorophenyl)-2′,3′,9′-trimethylspiro[cyclopropane-1,6′-thieno[3,2-f][1,2,4]triazolo[4,3-a][1,4]diazepine]-2-yl)methanol (Compound 210; 75 mg, 0.188 mmol) in DCM (2 mL) at 0° C. was added Dess-Martin periodinane (96 mg, 0.226 mmol). After 1 h at 0° C., extra Dess-Martin periodinane (96 mg, 0.226 mmol) was added, and the reaction was warmed to rt for 2 h. Then the reaction was diluted with diethylether and filtered. The filtrate was concentrated to dryness under vacuum, and the residue was used without purification in the next step. LRMS (M+H)+: 397 m/z.

Workup

  1. filtrationfiltered
  2. concentrationThe filtrate was concentrated to dryness under vacuum
  3. customthe residue was used without purification in the next step

Sources & evidence

ORD record
ord-c150d575cc0f442896713640d40a2e3f
Source dataset
uspto-grants-2016_02
Patent number
US09249161B2

Reaction notes

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