Sodium triacetoxyborohydride → HCID 9917154, compound

HRID 2268367Notes

Reaction equation

HRID 2268367 reaction equation
[NH2:1][CH2:2][C:3]1[N:11]=[C:10]2[C:6]([N:7]=[CH:8][N:9]2[C@H:12]2[C@H:16]([OH:17])[C@H:15]([OH:18])[C@@H:14]([CH2:19][O:20][CH3:21])[O:13]2)=[C:5]([NH:22][CH2:23][CH:24]([C:31]2[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=2)[C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)[N:4]=1.[CH3:37][O:38][CH2:39][C:40]1[CH:47]=[CH:46][CH:45]=[CH:44][C:41]=1[CH:42]=O.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>C(O)(=O)C.O1CCCC1>[C:25]1([CH:24]([C:31]2[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=2)[CH2:23][NH:22][C:5]2[N:4]=[C:3]([CH2:2][NH:1][CH2:42][C:41]3[CH:44]=[CH:45][CH:46]=[CH:47][C:40]=3[CH2:39][O:38][CH3:37])[N:11]=[C:10]3[C:6]=2[N:7]=[CH:8][N:9]3[C@H:12]2[C@H:16]([OH:17])[C@H:15]([OH:18])[C@@H:14]([CH2:19][O:20][CH3:21])[O:13]2)[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=1

Participants

6

Reactant 3

HCID 5049666Sodium triacetoxyborohydrideHCID 9897827(2R,3R,4S,5R)-2-{2-(Aminomethyl)-6-[(2,2-diphenylethyl)amino]-9H-purin-9-yl}-5-(methoxymethyl)tetrahydro-3,4-furandiolHCID 122456222-(METHOXYMETHYL)BENZALDEHYDE

Product 1

HCID 9917154HCID 9917154, compoundYield 60.6%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidCatalystHCID 8028TetrahydrofuranSolvent

Procedure

A solution of (2R,3R,4S,5R)-2-{2-(aminomethyl)-6-[(2,2-diphenylethyl)amino}-9H-purin-9-yl}-5-(methoxymethyl)tetrahydro-3,4-furandiol (example 1) (323 mg, 0.66 mmol), 2-(methoxymethyl)benzaldehyde (109 mg, 0.73 mmol) (Tetrahedron 4739, 47, 1991) and 1 drop of acetic acid in tetrahydrofuran (15 ml) was stirred at room temperature for 24 hr. Sodium triacetoxyborohydride (310 mg, 1.45 mmol) was then added and the reaction mixture stirred for 1 hr. At this point the solvent was partially removed under reduced pressure and the residue partitioned between ethyl acetate and saturated aqueous sodium hydrogen carbonate solution. The solvent was removed from the organic layer under reduced pressure and the residue purified by column chromatography on silica gel eluting with a solvent system of dichloromethane:methanol (97:3) increasing in polarity to dichloromethane:methanol:ammonia (95:5:0.5). This gave the title compound (250 mg) as a foam. MS: 625 (MH+).

Workup

  1. customAt this point the solvent was partially removed under reduced pressure
  2. customthe residue partitioned between ethyl acetate and saturated aqueous sodium hydrogen carbonate solution
  3. customThe solvent was removed from the organic layer under reduced pressure
  4. customthe residue purified by column chromatography on silica gel eluting with a solvent system of dichloromethane:methanol (97:3)
  5. temperatureincreasing in polarity to dichloromethane:methanol:ammonia (95:5:0.5)

Sources & evidence

ORD record
ord-fb5018724da3440ca0524ff695d5dfc5
Source dataset
uspto-grants-2001_12
Patent number
US06326359B1

Reaction notes

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