Cyclohexanecarboxaldehyde → (2R,3R,4S,5R)-2-[2-{[(Cyclohexylmethyl)amino]methyl}-6-[(2,2-diphenylethyl)amino]-9H-purin-9-yl]-5-(methoxymethyl)tetrahydro-3,4-furandiol

HRID 2268346Notes

Reaction equation

HRID 2268346 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.[CH:37]1([CH:43]=O)[CH2:42][CH2:41][CH2:40][CH2:39][CH2:38]1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>>[CH:37]1([CH2:43][NH:1][CH2:2][C:3]2[N:11]=[C:10]3[C:6]([N:7]=[CH:8][N:9]3[C@H:12]3[C@H:16]([OH:17])[C@H:15]([OH:18])[C@@H:14]([CH2:19][O:20][CH3:21])[O:13]3)=[C:5]([NH:22][CH2:23][CH:24]([C:31]3[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=3)[C:25]3[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=3)[N:4]=2)[CH2:42][CH2:41][CH2:40][CH2:39][CH2:38]1

Participants

4

Reactant 3

HCID 16275CyclohexanecarboxaldehydeHCID 5049666Sodium triacetoxyborohydrideHCID 9897827(2R,3R,4S,5R)-2-{2-(Aminomethyl)-6-[(2,2-diphenylethyl)amino]-9H-purin-9-yl}-5-(methoxymethyl)tetrahydro-3,4-furandiol

Product 1

HCID 10188624(2R,3R,4S,5R)-2-[2-{[(Cyclohexylmethyl)amino]methyl}-6-[(2,2-diphenylethyl)amino]-9H-purin-9-yl]-5-(methoxymethyl)tetrahydro-3,4-furandiolYield 46.9%

Procedure

The title compound was prepared by a similar method to example 5 from (2R,3R,4S,5R)-2-{2-(aminomethyl)-6-[(2,2-diphenylethyl)amino]-9H-purin-9-yl}-5-(methoxymethyl)tetrahydro-3,4-furandiol (example 1) (110 mg, 0.22 mmol), cyclohexanecarboxaldehyde (22 mg, 0.20 mmol) and sodium tnacetoxyborohydnde (70 mg, 0.33 mmol) to afford the title compound as a solid (55 mg). MS: 587 (MH+).

Sources & evidence

ORD record
ord-7e5ad5fb2911478fb6a59b44ccfc921d
Source dataset
uspto-grants-2001_12
Patent number
US06326359B1

Reaction notes

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