Lithium borohydride → HCID 18173064, compound

HRID 395893Notes

Reaction equation

HRID 395893 reaction equation
C[O:2][C:3]([CH:5]1[CH:11]([C:12](OC)=[O:13])[CH:10]2[O:16][CH:6]1[CH2:7][C:8]([C:18]1[N:26](C3CCCCO3)[C:25]3[C:24](=[O:33])[N:23]([CH2:34][CH2:35][CH3:36])[C:22](=[O:37])[N:21]([CH2:38][CH2:39][CH3:40])[C:20]=3[N:19]=1)([OH:17])[CH2:9]2)=O.[Li+].[BH4-]>C1COCC1>[OH:17][C:8]1([C:18]2[NH:26][C:25]3[C:24](=[O:33])[N:23]([CH2:34][CH2:35][CH3:36])[C:22](=[O:37])[N:21]([CH2:38][CH2:39][CH3:40])[C:20]=3[N:19]=2)[CH2:7][CH:6]2[O:16][CH:10]([CH:11]([CH2:12][OH:13])[CH:5]2[CH2:3][OH:2])[CH2:9]1

Participants

4

Reactant 2

HCID 4148881Lithium borohydrideHCID 69267943HCID 69267943, compound

Product 1

HCID 18173064HCID 18173064, compoundYield 110.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 3-[2,6-dioxo-1,3-dipropyl-7-(tetrahydropyran-2-yl)-2,3,6,7-tetrahydro-1H-purin-8-yl]-3-hydroxy-8-oxa-bicyclo[3.2.1]octane-6,7-dicarboxylic acid dimethyl ester (Example 53) (0.060 mmol, 0.030 g) in THF (3 ml) was added a solution of LiBH4 (2M, 0.050 ml). The reaction was stirred at room temperature 3d. It was then carefully quenched by addition of 1N HCl and extracted with EtOAc. The combined organic extracts were washed with saturated NaHCO3 (1X) and brine, and dried (MgSO4). Filtration and evaporation provided the desired product (0.028 g, 92%) as an oil. MS (ESP+, 60V): 529.7 (M+Na, 20%), 507.32 (M+H, 43%), 423.20 (87%), 223.08 (100%).

Workup

  1. customIt was then carefully quenched by addition of 1N HCl
  2. extractionextracted with EtOAc
  3. washThe combined organic extracts were washed with saturated NaHCO3 (1X) and brine
  4. dry with materialdried (MgSO4)
  5. filtrationFiltration and evaporation

Sources & evidence

ORD record
ord-e790337d0bd440a48bec43a2a2eaed14
Source dataset
uspto-grants-2003_08
Patent number
US06605600B1

Reaction notes

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