Sodium triacetoxyborohydride → (S)-2-(((5-(benzyloxymethyl)-4-methoxy-5H-pyrrolo[3,2-d]pyrimidin-7-yl)methyl)((2,2-dimethyl-1,3-dioxolan-4-yl)methyl)amino)ethanol

HRID 533207Notes

Reaction equation

HRID 533207 reaction equation
[CH3:1][C:2]1([CH3:12])[O:6][C@@H:5]([CH2:7][NH:8][CH2:9][CH2:10][OH:11])[CH2:4][O:3]1.[CH2:13]([O:20][CH2:21][N:22]1[C:30]2[C:29]([O:31][CH3:32])=[N:28][CH:27]=[N:26][C:25]=2[C:24]([CH:33]=O)=[CH:23]1)[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>>[CH2:13]([O:20][CH2:21][N:22]1[C:30]2[C:29]([O:31][CH3:32])=[N:28][CH:27]=[N:26][C:25]=2[C:24]([CH2:33][N:8]([CH2:7][C@H:5]2[CH2:4][O:3][C:2]([CH3:12])([CH3:1])[O:6]2)[CH2:9][CH2:10][OH:11])=[CH:23]1)[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1

Participants

4

Reactant 3

HCID 5049666Sodium triacetoxyborohydrideHCID 25223884(S)-2-((2,2-dimethyl-1,3-dioxolan-4-yl)methylamino)ethanolHCID 577250835-(benzyloxymethyl)-4-methoxy-5H-pyrrolo[3,2-d]pyrimidine-7-carbaldehyde

Product 1

HCID 25223885(S)-2-(((5-(benzyloxymethyl)-4-methoxy-5H-pyrrolo[3,2-d]pyrimidin-7-yl)methyl)((2,2-dimethyl-1,3-dioxolan-4-yl)methyl)amino)ethanolYield 80%

Procedure

The product from Example 14.1 (0.048 g, 0.274 mmol) was reductively aminated with 5-(benzyloxymethyl)-4-methoxy-5H-pyrrolo[3,2-d]pyrimidine-7-carbaldehyde (0.081 g, 0.274 mmol) and sodium triacetoxyborohydride (0.075 g, 0.356 mmol) in the same way as described for the R-enantiomer in Example 13.2. to give (S)-2-(((5-(benzyloxymethyl)-4-methoxy-5H-pyrrolo[3,2-d]pyrimidin-7-yl)methyl)((2,2-dimethyl-1,3-dioxolan-4-yl)methyl)amino)ethanol (100 mg, 80%) as a colourless gum which slowly turned pale yellow. The 1H and 13C NMR were as described for the R-enantiomer in Example 13.2. +ESMS Found 457.2469 C24H33N4O5 (M+H)+ requires 457.2451.

Sources & evidence

ORD record
ord-dbcc19cfbe4948339943c9f2f82cc23f
Source dataset
uspto-grants-2014_10
Patent number
US08853224B2

Reaction notes

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