Acetic Acid → (2R,3R,4S,5R)-2-{2-[2-(Cyclohexylamino)ethyl]-6-[(2,2-diphenyl ethyl)amino]-9H-purin-9-yl}-5-(methoxymethyl)tetrahydro-3,4-furandiol

HRID 2268351Notes

Reaction equation

HRID 2268351 reaction equation
C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].C(O)(=O)C.[NH2:19][CH2:20][CH2:21][C:22]1[N:30]=[C:29]2[C:25]([N:26]=[CH:27][N:28]2[C@H:31]2[C@H:35]([OH:36])[C@H:34]([OH:37])[C@@H:33]([CH2:38][O:39][CH3:40])[O:32]2)=[C:24]([NH:41][CH2:42][CH:43]([C:50]2[CH:55]=[CH:54][CH:53]=[CH:52][CH:51]=2)[C:44]2[CH:49]=[CH:48][CH:47]=[CH:46][CH:45]=2)[N:23]=1.[C:56]1(=O)[CH2:61][CH2:60][CH2:59][CH2:58][CH2:57]1>ClCCl>[CH:56]1([NH:19][CH2:20][CH2:21][C:22]2[N:30]=[C:29]3[C:25]([N:26]=[CH:27][N:28]3[C@H:31]3[C@H:35]([OH:36])[C@H:34]([OH:37])[C@@H:33]([CH2:38][O:39][CH3:40])[O:32]3)=[C:24]([NH:41][CH2:42][CH:43]([C:50]3[CH:55]=[CH:54][CH:53]=[CH:52][CH:51]=3)[C:44]3[CH:45]=[CH:46][CH:47]=[CH:48][CH:49]=3)[N:23]=2)[CH2:61][CH2:60][CH2:59][CH2:58][CH2:57]1

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 7967CyclohexanoneHCID 5049666Sodium triacetoxyborohydrideHCID 9957801(2R,3R,4S,5R)-2-{2-(2-Aminoethyl)-6-[(2,2-diphenylethyl)amino]-9H-purin-9-yl}-5-(methoxymethyl)tetrahydro-3,4-furandiol

Product 1

HCID 9851372(2R,3R,4S,5R)-2-{2-[2-(Cyclohexylamino)ethyl]-6-[(2,2-diphenyl ethyl)amino]-9H-purin-9-yl}-5-(methoxymethyl)tetrahydro-3,4-furandiolYield 56.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

Sodium triacetoxyborohydride (75 mg, 0.35 mmol) and acetic acid (16 mg, 0.27 mmol) were added sequentially to a stirred solution of (2R,3R,4S,5R)-2-{2-(2-aminoethyl)-6-[(2,2-diphenylethyl)amino]-9H-purin-9-yl}-5-(methoxymethyl)tetrahydro-3,4-furandiol (example 11) (120 mg, 0.24 mmol) and cyclohexanone (23 mg, 0.235 mmol) in dichloromethane (15 ml). The resulting mixture was stirred at room temperature for 24 hr, diluted with dichloromethane and washed sequentially with a saturated aqueous solution of sodium hydrogen carbonate, water and brine. The organic phase was dried with anhydrous sodium sulfate, the solvent removed under reduced pressure and the residue purified by column chromatography on silica gel eluting with a gradient system of dichloromethane:methanol:ammonia (95:5:0.5) changing to dichloromethane:methanol:ammonia (90:10:1) to afford the title compound as a solid (78 mg). MS: 587 (MH+).

Workup

  1. washwashed sequentially with a saturated aqueous solution of sodium hydrogen carbonate, water and brine
  2. dry with materialThe organic phase was dried with anhydrous sodium sulfate
  3. customthe solvent removed under reduced pressure
  4. customthe residue purified by column chromatography on silica gel eluting with a gradient system of dichloromethane:methanol:ammonia (95:5:0.5)

Sources & evidence

ORD record
ord-2a85a83ec4214d248b88f3ca0439c7a5
Source dataset
uspto-grants-2001_12
Patent number
US06326359B1

Reaction notes

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