Veratraldehyde → HCID 9917413, compound

HRID 2268366Notes

Reaction equation

HRID 2268366 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][C:39]1[CH:40]=[C:41]([CH:44]=[CH:45][C:46]=1[O:47][CH3:48])[CH:42]=O.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>O1CCCC1>[CH3:37][O:38][C:39]1[CH:40]=[C:41]([CH:44]=[CH:45][C:46]=1[O:47][CH3:48])[CH2:42][NH: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:26]=[CH:27][CH:28]=[CH:29][CH:30]=2)[N:4]=1

Participants

5

Reactant 3

HCID 8419VeratraldehydeHCID 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 9917413HCID 9917413, compoundYield 35.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

(2R,3R,4S,5R)-2-{2-(Aminomethyl)-6-[(2,2-diphenylethyl)amino}-9H-purin-9-yl}-5-(methoxymethyl)tetrahydro-3,4-furandiol (example 1) (200 mg, 0.4 mmol) was dissolved in stirred tetrahydrofuran (5 ml) and 3,4-dimethoxybenzaldehyde (130 mg, 0.8 mmol) added. The reagents were stirred together until everything had dissolved and then sodium triacetoxyborohydride (130 mg, 0.6 mmol) added. The reaction mixture was stirred for 24 hr and then quenched by the addition of methanol (1 ml). The solvent was removed under reduced pressure and the residue purified by column chromatography on silica gel eluting with a solvent gradient of dichloromethane:methanol:ammonia (95:5:0.5) increasing to (92:7:1). This gave the title compound (90 mg) as a foam. MS: 641 (MH+).

Workup

  1. dissolutionhad dissolved
  2. stirringThe reaction mixture was stirred for 24 hr
  3. customquenched by the addition of methanol (1 ml)
  4. customThe solvent was removed under reduced pressure
  5. customthe residue purified by column chromatography on silica gel eluting with a solvent gradient of dichloromethane:methanol:ammonia (95:5:0.5)
  6. temperatureincreasing to (92:7:1)

Sources & evidence

ORD record
ord-97058604debf4223907ff18949587de9
Source dataset
uspto-grants-2001_12
Patent number
US06326359B1

Reaction notes

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