Formaldehyde → HCID 59734975, compound

HRID 746412Notes

Reaction equation

HRID 746412 reaction equation
[CH:1]([C@:4]1([C:16]([O:18][CH3:19])=[O:17])[CH2:8][CH2:7][C@@H:6]([NH:9][CH:10]2[CH2:15][CH2:14][O:13][CH2:12][CH2:11]2)[CH2:5]1)([CH3:3])[CH3:2].C=O.[C:22](O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>C(Cl)Cl>[CH:1]([C@:4]1([C:16]([O:18][CH3:19])=[O:17])[CH2:8][CH2:7][C@@H:6]([N:9]([CH3:22])[CH:10]2[CH2:15][CH2:14][O:13][CH2:12][CH2:11]2)[CH2:5]1)([CH3:3])[CH3:2]

Participants

5

Reactant 3

HCID 712FormaldehydeHCID 5049666Sodium triacetoxyborohydrideHCID 59735082HCID 59735082, compound

Product 1

HCID 59734975HCID 59734975, compoundYield 95.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

Methyl (1S,3R)-1-isopropyl-3-(tetrahydro-2H-pyran-4-ylamino)cyclopentanecarboxylate (1.0 g, 3.7 mmol) was combined with 37% aqueous formaldehyde solution (3.0 mL, 37 mmol) in 50 mL of DCM. After stirring for 35 min, 4 Å powdered molecular sieves, and sodium triacetoxyborohydride (3.9 g, 19 mmol) were added and the reaction mixture was stirred overnight under a nitrogen atmosphere. The reaction mixture was diluted with DCM, filtered through celite, and the filtrate was washed with saturated NaHCO3 solution, and brine. The organic layer was dried over anhydrous MgSO4, filtered, and concentrated to afford 1.0 g of methyl (1S,3R)-1-isopropyl-3-[methyl(tetrahydro-2H-pyran-4-yl)amino]cyclopentanecarboxylate.

Workup

  1. additionwere added
  2. stirringthe reaction mixture was stirred overnight under a nitrogen atmosphere
  3. filtrationfiltered through celite
  4. washthe filtrate was washed with saturated NaHCO3 solution, and brine
  5. dry with materialThe organic layer was dried over anhydrous MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-aad68996a9854680ad17963e6dcedf69
Source dataset
uspto-grants-2008_07
Patent number
US07393844B2

Reaction notes

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