Sodium triacetoxyborohydride → HCID 59605340, compound

HRID 1945697Notes

Reaction equation

HRID 1945697 reaction equation
[Cl:1][C:2]1[N:10]=[C:9]2[C:5]([N:6]=[C:7]([CH:12]=O)[N:8]2[CH3:11])=[C:4]([N:14]2[CH:19]3[CH2:20][CH2:21][CH:15]2[CH2:16][O:17][CH2:18]3)[N:3]=1.[NH:22]1[CH2:27][CH2:26][CH:25]([C:28]([OH:31])([CH3:30])[CH3:29])[CH2:24][CH2:23]1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>ClCCCl>[Cl:1][C:2]1[N:10]=[C:9]2[C:5]([N:6]=[C:7]([CH2:12][N:22]3[CH2:27][CH2:26][CH:25]([C:28]([OH:31])([CH3:30])[CH3:29])[CH2:24][CH2:23]3)[N:8]2[CH3:11])=[C:4]([N:14]2[CH:19]3[CH2:20][CH2:21][CH:15]2[CH2:16][O:17][CH2:18]3)[N:3]=1

Participants

5

Reactant 3

HCID 5049666Sodium triacetoxyborohydrideHCID 52003212-(4-Piperidyl)-2-propanolHCID 59606042HCID 59606042, compound

Product 1

HCID 59605340HCID 59605340, compoundYield 82%

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

A mixture of 2-chloro-9-methyl-6-(3-oxa-8-azabicyclo[3.2.1]oct-8-yl)-9H-purine-8-carbaldehyde (500 mg, 1.63 mmol), 2-piperidin-4-ylpropan-2-ol (256 mg, 1.79 mmol) and 4 Å powdered molecular sieves (500 mg) in DCE (11 mL) was stirred for 4 h before the addition of sodium triacetoxyborohydride (690 mg, 3.26 mmol). The resulting mixture was allowed to stir for 17 h then filtered through Celite®, washing with MeOH. The resulting filtrate was loaded onto an Isolute® SCX-2 cartridge which was washed with MeOH and the product eluted with 2M NH3/MeOH/DCM. The resulting residue was purified by column chromatography (Si—PCC, MeOH:DCM, 0-10%) affording the title compound as a pale yellow solid (577 mg, 82%). LCMS (method H): RT 0.30 and 2.00 min [M+H]+ 435.4

Workup

  1. filtrationthen filtered through Celite®
  2. washwashing with MeOH
  3. washwas washed with MeOH
  4. washthe product eluted with 2M NH3/MeOH/DCM
  5. customThe resulting residue was purified by column chromatography (Si—PCC, MeOH:DCM, 0-10%)

Sources & evidence

ORD record
ord-dfc9566192f04e19aeccb8a4569f87e3
Source dataset
uspto-grants-2013_03
Patent number
US08394796B2

Reaction notes

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