Formaldehyde → HCID 67992742, compound

HRID 712423Notes

Reaction equation

HRID 712423 reaction equation
[CH2:1]([N:8]1[CH2:13][CH2:12][O:11][CH:10]2[CH2:14][N:15]([C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18])[CH2:16][CH:9]12)C1C=CC=CC=1.C=O>CCO.CC#N.[OH-].[OH-].[Pd+2]>[C:20]([O:19][C:17]([N:15]1[CH2:16][CH:9]2[CH:10]([O:11][CH2:12][CH2:13][N:8]2[CH3:1])[CH2:14]1)=[O:18])([CH3:23])([CH3:22])[CH3:21]

Participants

6

Reactant 2

HCID 712FormaldehydeHCID 19594624HCID 19594624, compound

Product 1

HCID 67992742HCID 67992742, compoundYield 43.42%

Reagents, catalysts & solvents 3

HCID 9942167Palladium hydroxideCatalystHCID 702EthanolSolventHCID 6342AcetonitrileSolvent

Procedure

To a solution of tert-butyl 4-benzylhexahydropyrrolo[3,4-b][1,4]oxazine-6(2H)-carboxylate (1.00 g) in EtOH (20 mL) was added 20% Pd(OH)2/C (0.30 g). The reaction mixture was heated to reflux for 8 h and filtered. The filtrate was evaporated in vacuo. To a solution of the residue in CH3CN (30 mL) was added formaldehyde aqueous solution (15 eq) and NaB(OCOCH3)3H (2.5 eq). The mixture was stirred at room temperature for 6 h under N2. The solvent of the mixture was removed under reduce vacuum pressure, and the residue was chromatographed with a silica gel column to give the title compound (0.33 g, 43.42%). The compound was characterized by the following spectroscopic data: MS (ESI, pos. ion) m/z: 243.3 (M+1).

Workup

  1. temperatureThe reaction mixture was heated
  2. temperatureto reflux for 8 h
  3. filtrationfiltered
  4. customThe filtrate was evaporated in vacuo
  5. customThe solvent of the mixture was removed
  6. customthe residue was chromatographed with a silica gel column

Sources & evidence

ORD record
ord-4b97e66a30bc46808731300c63cdc29c
Source dataset
uspto-grants-2015_11
Patent number
US09181277B2

Reaction notes

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