Hydrochloric Acid → HCID 66906535, compound

HRID 1689624Notes

Reaction equation

HRID 1689624 reaction equation
[BH4-].[Na+].[C:3]([C:6]1[N:7]([C:17]2[N:18]=[CH:19][N:20]=[C:21]([NH2:24])[C:22]=2[N:23]=1)[C@@H:8]1[O:16][C@H:13]([CH2:14][OH:15])[C@@H:11]([OH:12])[C@H:9]1[OH:10])(=[O:5])[CH3:4].Cl>C1COCC1.CO.C(Cl)Cl>[OH:5][CH:3]([C:6]1[N:7]([C:17]2[N:18]=[CH:19][N:20]=[C:21]([NH2:24])[C:22]=2[N:23]=1)[C@@H:8]1[O:16][C@H:13]([CH2:14][OH:15])[C@@H:11]([OH:12])[C@H:9]1[OH:10])[CH3:4]

Participants

7

Reactant 3

HCID 313Hydrochloric AcidHCID 4311764Sodium borohydrideHCID 66906212HCID 66906212, compound

Product 1

HCID 66906535HCID 66906535, compound

Reagents, catalysts & solvents 3

HCID 887MethanolSolvent2×HCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolvent

Procedure

NaBH4 (0.19 g, 5.05 mmol) was added to a solution of 8-acetyladenosine (17l) (0.78 g, 2.52 mmol) in THF (35 ml) and MeOH (4 ml) under argon and the mixture stirred at room temperature for 18 h. The mixture was treated dropwise with 1 M HCl until neutral pH and the mixture applied on top of a flash chromatography column which was developed by 30% MeOH in CH2Cl2; yield 0.46 g (59%). The product was a mixture of the two alcohol epimers, ratio 1:1.

Sources & evidence

ORD record
ord-9de37079eb3a4772b6bb4f4ff8bc5995
Source dataset
uspto-grants-2012_04
Patent number
US08153609B2

Reaction notes

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