Formaldehyde → HCID 90417130, compound

HRID 1484805Notes

Reaction equation

HRID 1484805 reaction equation
Cl.[C:2]1([C:8]2[CH2:13][NH:12][CH2:11][CH2:10][C:9]=2[CH2:14][OH:15])[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH3:16]CN(CC)CC.C=O.[BH-](OC(C)=O)(OC(C)=O)OC(C)=O.[Na+]>C(#N)C>[CH3:16][N:12]1[CH2:13][C:8]([C:2]2[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=2)=[C:9]([CH2:14][OH:15])[CH2:10][CH2:11]1

Participants

6

Reactant 4

HCID 712FormaldehydeHCID 8471TriethylamineHCID 5049666Sodium triacetoxyborohydrideHCID 90415992HCID 90415992, compound

Product 1

HCID 90417130HCID 90417130, compoundYield 66.2%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a solution of (5-phenyl-1,2,3,6-tetrahydropyridin-4-yl)methanol hydrochloride (230 mg, 1.04 mmol) in ACN (10 mL) was added Et3N (0.15 mL, 1.04 mmol) followed by formalin (340 mg, 4.16 mmol). After stirred at room temperature for 10 min, it was added Na(OAc)3BH (440 mg, 2.08 mmol) and was stirred for 30 min, the mixture was concentrated to remove most of the ACN, and the residue was diluted with CHCl3, organic layer was washed with Sat. NaHCO3, brine, dried and concentrated to give crude product, which was purified by column (DCM/MeOH=9:1) to give (1-methyl-5-phenyl-1,2,3,6-tetrahydropyridin-4-yl)methanol (140 mg).

Workup

  1. stirringwas stirred for 30 min
  2. concentrationthe mixture was concentrated
  3. customto remove most of the ACN
  4. additionthe residue was diluted with CHCl3, organic layer
  5. washwas washed with Sat. NaHCO3, brine
  6. customdried
  7. concentrationconcentrated
  8. customto give crude product, which
  9. customwas purified by column (DCM/MeOH=9:1)

Sources & evidence

ORD record
ord-a8c756e1737344e0b1ce8719092f13b5
Source dataset
uspto-grants-2016_08
Patent number
US09422279B2

Reaction notes

Loading…