Triacetoxyperiodinane → HCID 86717557, compound

HRID 712104Notes

Reaction equation

HRID 712104 reaction equation
[OH:1][C@@H:2]([C:4]1[N:15]([C@@H:16]2[CH2:21][O:20][C@@H:19]([CH2:22][C:23]#[N:24])[CH2:18][CH2:17]2)[C:7]2=[C:8]3[S:14][CH:13]=[CH:12][C:9]3=[N:10][CH:11]=[C:6]2[N:5]=1)[CH3:3].C(=O)(O)[O-].[Na+].CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O>C(Cl)Cl>[C:2]([C:4]1[N:15]([C@@H:16]2[CH2:21][O:20][C@@H:19]([CH2:22][C:23]#[N:24])[CH2:18][CH2:17]2)[C:7]2=[C:8]3[S:14][CH:13]=[CH:12][C:9]3=[N:10][CH:11]=[C:6]2[N:5]=1)(=[O:1])[CH3:3]

Participants

5

Reactant 3

HCID 159087TriacetoxyperiodinaneHCID 516892Sodium BicarbonateHCID 73776047HCID 73776047, compound

Product 1

HCID 86717557HCID 86717557, compoundYield 163.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of ((2R,5S)-5-{2-[(1R)-1-hydroxyethyl]-1H-imidazo[4,5-d]thieno[3,2-b]pyridin-1-yl}tetrahydro-2H-pyran-2-yl)acetonitrile (154 mg, 0.450 mmol) in methylene chloride (2.0 mL) was added sodium bicarbonate (110 mg, 1.31 mmol) followed by Dess-Martin periodinane (219 mg, 0.517 mmol). The resulting mixture was stirred at room temperature for 3 h. The mixture was diluted with dichloromethane, filtered, and concentrated. The crude was purified on silica gel, eluted with 0-10% MeOH in dichloromethane to give 250 mg of crude product as a white gum. LCMS calculated for C17H17N4O2S (M+H)+: m/z=341.1. Found: 341.0 (M+H). 1H NMR (400 MHz, CDCl3) δ 9.23 (s, 1H), 7.77 (s, 2H), 4.52 (t, J=11.1 Hz, 1H), 4.07 (dd, J=10.1 and 4.4 Hz, 2H), 2.92-2.81 (m, 3H), 2.70-2.64 (m, 2H), 2.21-2.09 (m, 2H), 1.83 (qd, J=13.4 and 4.7 Hz, 1H), 1.62 (s, 2H) ppm.

Workup

  1. filtrationfiltered
  2. concentrationconcentrated
  3. customThe crude was purified on silica gel
  4. washeluted with 0-10% MeOH in dichloromethane

Sources & evidence

ORD record
ord-acd0a250daa34941ac33bd77c1fefd6e
Source dataset
uspto-grants-2015_11
Patent number
US09181271B2

Reaction notes

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