Formaldehyde → 6-Benzyl-1-methyloctahydropyrrolo[3,4-b]pyridine

HRID 712459Notes

Reaction equation

HRID 712459 reaction equation
[CH2:1]([N:8]1[CH2:16][CH:15]2[CH:10]([NH:11][CH2:12][CH2:13][CH2:14]2)[CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH2:17]=O.[OH-].[Na+]>C(O)=O>[CH2:1]([N:8]1[CH2:16][CH:15]2[CH:10]([N:11]([CH3:17])[CH2:12][CH2:13][CH2:14]2)[CH2:9]1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 712FormaldehydeHCID 14798Sodium HydroxideHCID 113563766-Benzyloctahydro-1H-pyrrolo[3,4-b]pyridine

Product 1

HCID 150700086-Benzyl-1-methyloctahydropyrrolo[3,4-b]pyridineYield 45%

Reagents, catalysts & solvents 1

HCID 284Formic AcidSolvent

Procedure

A solution of 6-benzyloctahydro-1H-pyrrolo[3,4-b]pyridine (2.00 g) and 37% HCHO (6.0 mL) in HCO2H was heated to 90° C. and stirred for 4 h. The reaction mixture was cooled to rt and poured into ice-water. The mixture was adjusted to pH 10 with 2M NaOH aqueous solution and extracted with CH2Cl2 (70 mL×3). The combined organic phases were dried over anhydrous Na2SO4 and filtered. The filtrate was concentrated in vacuo and the residue was chromatographed with a silica gel column (eluting agent: 20:1 (v/v) DCM/MeOH) to give the title compound as pale yellow oil (0.95 g, 45.00%), HPLC: 85.00%. The compound was characterized by the following spectroscopic data: MS (ESI, pos. ion) m/z: 231.2 (M+1).

Workup

  1. extractionextracted with CH2Cl2 (70 mL×3)
  2. dry with materialThe combined organic phases were dried over anhydrous Na2SO4
  3. filtrationfiltered
  4. concentrationThe filtrate was concentrated in vacuo
  5. customthe residue was chromatographed with a silica gel column (eluting agent: 20:1 (v/v) DCM/MeOH)

Sources & evidence

ORD record
ord-28438f15f21d400c9a2537d9d40c9146
Source dataset
uspto-grants-2015_11
Patent number
US09181277B2

Reaction notes

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