Water → {9-[(2R,3R,4R,5R)-3,4-Bis{[tert-butyl(dimethyl)silyl]oxy}-5-(methoxymethyl)tetrahydro-2-furanyl]-6-[(2,2-diphenylethyl)amino]-9H-purin-2-yl}methanol

HRID 2268410Notes

Reaction equation

HRID 2268410 reaction equation
[Si:1]([O:8][C@@H:9]1[C@H:13]([O:14][Si:15]([C:18]([CH3:21])([CH3:20])[CH3:19])([CH3:17])[CH3:16])[C@@H:12]([CH2:22][O:23][CH3:24])[O:11][C@H:10]1[N:25]1[CH:33]=[N:32][C:31]2[C:26]1=[N:27][C:28]([C:49](OC)=[O:50])=[N:29][C:30]=2[NH:34][CH2:35][CH:36]([C:43]1[CH:48]=[CH:47][CH:46]=[CH:45][CH:44]=1)[C:37]1[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=1)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].B(OC)(OC)OC.[BH4-].[Li+].O>C(OCC)C>[Si:1]([O:8][C@@H:9]1[C@H:13]([O:14][Si:15]([C:18]([CH3:19])([CH3:20])[CH3:21])([CH3:17])[CH3:16])[C@@H:12]([CH2:22][O:23][CH3:24])[O:11][C@H:10]1[N:25]1[CH:33]=[N:32][C:31]2[C:26]1=[N:27][C:28]([CH2:49][OH:50])=[N:29][C:30]=2[NH:34][CH2:35][CH:36]([C:37]1[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=1)[C:43]1[CH:48]=[CH:47][CH:46]=[CH:45][CH:44]=1)([C:4]([CH3:6])([CH3:7])[CH3:5])([CH3:2])[CH3:3]

Participants

6

Reactant 4

HCID 962WaterHCID 8470Trimethyl borateHCID 4148881Lithium borohydrideHCID 69534083methyl 9-[(2R,3R,4R,5R)-3,4-bis{[tert-butyl(dimethyl)silyl]oxy}-5-(methoxymethyl)tetrahydro-2-furanyl]-6-[(2,2-diphenylethyl)amino]-9H-purine-2-carboxylate

Product 1

HCID 69534107{9-[(2R,3R,4R,5R)-3,4-Bis{[tert-butyl(dimethyl)silyl]oxy}-5-(methoxymethyl)tetrahydro-2-furanyl]-6-[(2,2-diphenylethyl)amino]-9H-purin-2-yl}methanolYield 74.5%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

A stirred solution of methyl 9-[(2R,3R,4R,5R)-3,4-bis{[tert-butyl(dimethyl)silyl]oxy}-5-(methoxymethyl)tetrahydro-2-furanyl]-6-[(2,2-diphenylethyl)amino]-9H-purine-2-carboxylate (7.2 g, 9.64 mmol) (preparation 14) in dry diethyl ether (150 ml) was treated with trimethyl borate (0.11 ml, 0.97 mmol) and lithium borohydride (212 mg, 9.64 mmol) and the mixture heated at reflux for 1 hr under a nitrogen atmosphere. The mixture was then cooled to room temperature, water (100 ml) carefully added and stirring continued for 10 minutes. The organic phase was separated, washed with brine and dried with anhydrous sodium sulfate. The solvent was removed under reduced pressure and the residue purified by column chromatography on silica gel eluting with a gradient system of diethyl ether:pentane (1:1) changing to diethyl ether:pentane (3:1) to afford the title compound as an oil (5.17 g). MS: 721 (MH+).

Workup

  1. temperaturethe mixture heated
  2. temperatureat reflux for 1 hr under a nitrogen atmosphere
  3. customThe organic phase was separated
  4. washwashed with brine
  5. dry with materialdried with anhydrous sodium sulfate
  6. customThe solvent was removed under reduced pressure
  7. customthe residue purified by column chromatography on silica gel eluting with a gradient system of diethyl ether:pentane (1:1)

Sources & evidence

ORD record
ord-da4969d885ed4dc49553fe498d50b842
Source dataset
uspto-grants-2001_12
Patent number
US06326359B1

Reaction notes

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