Cyclopropanecarboxaldehyde → N-(9-[(2R,3R,4R,5R)-3,4-Bis{[tert-butyl(dimethyl)silyl]oxy}-5-(methoxymethyl)tetrahydro-2-furanyl]-2-{2-[(cyclopropylmethyl)amino]ethyl}-9H-purin-6-yl)-N-(2,2-diphenylethyl)amine

HRID 2268425Notes

Reaction equation

HRID 2268425 reaction equation
[NH2:1][CH2:2][CH2:3][C:4]1[N:12]=[C:11]2[C:7]([N:8]=[CH:9][N:10]2[C@H:13]2[C@H:17]([O:18][Si:19]([C:22]([CH3:25])([CH3:24])[CH3:23])([CH3:21])[CH3:20])[C@H:16]([O:26][Si:27]([C:30]([CH3:33])([CH3:32])[CH3:31])([CH3:29])[CH3:28])[C@@H:15]([CH2:34][O:35][CH3:36])[O:14]2)=[C:6]([NH:37][CH2:38][CH:39]([C:46]2[CH:51]=[CH:50][CH:49]=[CH:48][CH:47]=2)[C:40]2[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=2)[N:5]=1.[CH:52]1([CH:55]=O)[CH2:54][CH2:53]1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>O1CCCC1>[Si:19]([O:18][C@@H:17]1[C@H:16]([O:26][Si:27]([C:30]([CH3:31])([CH3:32])[CH3:33])([CH3:29])[CH3:28])[C@@H:15]([CH2:34][O:35][CH3:36])[O:14][C@H:13]1[N:10]1[CH:9]=[N:8][C:7]2[C:11]1=[N:12][C:4]([CH2:3][CH2:2][NH:1][CH2:55][CH:52]1[CH2:54][CH2:53]1)=[N:5][C:6]=2[NH:37][CH2:38][CH:39]([C:40]1[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=1)[C:46]1[CH:47]=[CH:48][CH:49]=[CH:50][CH:51]=1)([C:22]([CH3:23])([CH3:24])[CH3:25])([CH3:21])[CH3:20]

Participants

5

Reactant 3

HCID 123114CyclopropanecarboxaldehydeHCID 5049666Sodium triacetoxyborohydrideHCID 69534061N-{2-(2-Aminoethyl)-9-[(2R,3R,4R,5R)-3,4-bis{[tert-butyl(dimethyl)silyl]oxy}-5-(methoxymethyl)tetrahydro-2-furanyl]-9H-purin-6-yl}-N-(2,2-diphenylethyl)amine

Product 1

HCID 69534146N-(9-[(2R,3R,4R,5R)-3,4-Bis{[tert-butyl(dimethyl)silyl]oxy}-5-(methoxymethyl)tetrahydro-2-furanyl]-2-{2-[(cyclopropylmethyl)amino]ethyl}-9H-purin-6-yl)-N-(2,2-diphenylethyl)amineYield 78.8%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

The title compound was prepared by a similar method to example 5 from N-{2-(2-aminoethyl)-9-[(2R,3R,4R,5R)-3,4-bis{[tert-butyl(dimethyl)silyl]oxy}-5-(methoxymethyl)tetrahydro-2-furanyl]-9H-purin-6-yl)-N-(2,2-diphenylethyl)amine (430 mg, 0.58 mmol) (preparation 18), cyclopropanecarbaldehyde (45 mg, 0.64 mmol) and sodium triacetoxyborohydride (270 mg, 1.27 mmol) in tetrahydrofuran (10 ml). The product was purified by column chromatography on silica gel eluting with a solvent gradient of dichloromethane rising in polarity to dichloromethane:methanol:ammonia (95:5:0.5) to give the title compound (360 mg) as a gum. MS: 788 (MH+).

Workup

  1. customThe product was purified by column chromatography on silica gel eluting with a solvent gradient of dichloromethane rising in polarity to dichloromethane:methanol:ammonia (95:5:0.5)

Sources & evidence

ORD record
ord-6bfec0e47f164281aa2abea85f808c0e
Source dataset
uspto-grants-2001_12
Patent number
US06326359B1

Reaction notes

Loading…