Acetic Acid → [5-Chloro-4-(tetrahydro-pyran-2-yloxymethyl)-pyridin-3-ylmethyl]-(2,2-dimethyl-[1,3]dioxolan-4-ylmethyl)-amine

HRID 1959592Notes

Reaction equation

HRID 1959592 reaction equation
C(O)(=O)C.[BH3-]C#N.[Na+].[Cl:9][C:10]1[C:11]([CH2:18][O:19][CH:20]2[CH2:25][CH2:24][CH2:23][CH2:22][O:21]2)=[C:12]([CH:16]=O)[CH:13]=[N:14][CH:15]=1.[CH3:26][C:27]1([CH3:34])[O:31][CH:30]([CH2:32][NH2:33])[CH2:29][O:28]1>CO>[Cl:9][C:10]1[C:11]([CH2:18][O:19][CH:20]2[CH2:25][CH2:24][CH2:23][CH2:22][O:21]2)=[C:12]([CH2:16][NH:33][CH2:32][CH:30]2[CH2:29][O:28][C:27]([CH3:34])([CH3:26])[O:31]2)[CH:13]=[N:14][CH:15]=1

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 41223491,3-Dioxolane-4-methanamine, 2,2-dimethyl-HCID 5003444Sodium cyanoborohydrideHCID 441904745-Chloro-4-(tetrahydro-pyran-2-yloxymethyl)-pyridine-3-carbaldehyde

Product 1

HCID 67077614[5-Chloro-4-(tetrahydro-pyran-2-yloxymethyl)-pyridin-3-ylmethyl]-(2,2-dimethyl-[1,3]dioxolan-4-ylmethyl)-amine

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Acetic acid (133 μL) and NaBH3CN (14.8 mg, 0.235 mmol) were added to a stirred solution of 5-chloro-4-(tetrahydro-pyran-2-yloxymethyl)-pyridine-3-carbaldehyde (40 mg, 0.157 mmol) and 2,2-dimethyl-1,3-dioxolane-4-methanamine (203 μL, 1.57 mmol) in MeOH (1 mL). After stirring for 2 h at room temperature the solvent was removed in vacuo and the residue was partitioned between DCM (10 mL) and saturated NaHCO3 solution (10 mL). After extraction of the aqueous layer with DCM (2×10 mL) the combined organic layers were dried over Na2SO4, filtered, and concentrated in vacuo. The resulting title compound was used for the next reaction without purification. MS (m/z): 370.9 [M+H+].

Workup

  1. customwas removed in vacuo
  2. customthe residue was partitioned between DCM (10 mL) and saturated NaHCO3 solution (10 mL)
  3. extractionAfter extraction of the aqueous layer with DCM (2×10 mL) the combined organic layers
  4. dry with materialwere dried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customThe resulting title compound was used for the next reaction without purification

Sources & evidence

ORD record
ord-d243385d15174455806e5f9d7a8caae5
Source dataset
uspto-grants-2013_04
Patent number
US08410134B2

Reaction notes

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