Ethanol → HCID 86607302, compound

HRID 552700Notes

Reaction equation

HRID 552700 reaction equation
[C:1]([O:4][C@H:5]1[C@H:9]([O:10][C:11](=[O:13])[CH3:12])[C@@H:8]([CH2:14][O:15][Si:16]([CH:23]([CH3:25])[CH3:24])([CH:20]([CH3:22])[CH3:21])[CH:17]([CH3:19])[CH3:18])[O:7][C@H:6]1[N:26]1[CH:34]=[N:33][C:32]2[C:27]1=[N:28][CH:29]=[N:30][C:31]=2Br)(=[O:3])[CH3:2].C([N:38]([CH2:41][CH3:42])CC)C.[CH2:43](O)[CH3:44]>>[C:1]([O:4][C@H:5]1[C@H:9]([O:10][C:11](=[O:13])[CH3:12])[C@@H:8]([CH2:14][O:15][Si:16]([CH:23]([CH3:25])[CH3:24])([CH:20]([CH3:22])[CH3:21])[CH:17]([CH3:19])[CH3:18])[O:7][C@H:6]1[N:26]1[CH:34]=[N:33][C:32]2[C:27]1=[N:28][CH:29]=[N:30][C:31]=2[NH:38][C@@H:41]1[C:42]2[C:9](=[CH:5][CH:6]=[CH:43][CH:44]=2)[CH2:8][CH2:14]1)(=[O:3])[CH3:2]

Participants

4

Reactant 3

HCID 702EthanolHCID 8471TriethylamineHCID 86607300HCID 86607300, compound

Product 1

HCID 86607302HCID 86607302, compound

Procedure

(2R,3S,4R,5R)-2-(6-Bromo-9H-purin-9-yl)-5-{[(triisopropylsilyl)oxy]methyl}-tetrahydrofuran-3,4-diyl diacetate (0.402 g, 0.703 mmol) was stirred in ethanol (10 mL) and S-(+)-1-aminoindan (0.14 mL, 1.06 mmol) was added followed by triethylamine (0.2 mL, 1.41 mmol). The reaction mixture was heated at overnight. The brown solution was concentrated and purified by flash chromatography, eluting with 10 to 35% ethyl acetate/hexanes to give the title compound as a white solid (0.142 g) and deacylated product (0.161 g, 37%).

Workup

  1. temperatureThe reaction mixture was heated at overnight
  2. concentrationThe brown solution was concentrated
  3. custompurified by flash chromatography
  4. washeluting with 10 to 35% ethyl acetate/hexanes

Sources & evidence

ORD record
ord-aa07270ec1d74673b53a524be58cb065
Source dataset
uspto-grants-2011_05
Patent number
US07951810B2

Reaction notes

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