Formaldehyde → HCID 66936435, compound

HRID 1366440Notes

Reaction equation

HRID 1366440 reaction equation
[NH2:1][C@H:2]1[C@H](C)[CH2:5][N:4]([C:8](OC(C)(C)C)=O)[CH2:3]1.[CH2:15]=O.[BH-](O[C:27]([CH3:29])=O)(OC(C)=O)OC(C)=O.[Na+].[OH-].[Na+]>C1COCC1.Cl.O1CCOCC1>[CH3:5][N:4]([CH3:8])[C@H:3]1[C@H:27]([CH3:29])[CH2:15][NH:1][CH2:2]1

Participants

8

Reactant 4

HCID 712FormaldehydeHCID 14798Sodium HydroxideHCID 5049666Sodium triacetoxyborohydrideHCID 86309414trans-1-Boc-3-amino-4-methylpyrrolidine

Product 1

HCID 66936435HCID 66936435, compound

Reagents, catalysts & solvents 3

HCID 313Hydrochloric AcidSolventHCID 8028TetrahydrofuranSolventHCID 312751,4-DioxaneSolvent

Procedure

A solution of commercially available 1,1-dimethylethyl(trans)-3-amino-4-methyl-1-pyrrolidinecarboxylate (1 g, 5 mmol) and formaldehyde (0.69 mL, 25 mmol, 37% in water) in THF (20 mL) was stirred at room temperature for 1 hour. NaBH(OAc)3 (7.4 g, 35 mmol) was added and the reaction was stirred overnight. 1 M NaOH (20 mL) was added and the layers were allowed to separate. The aqueous phase was extracted with ether and the combined organics were dried over sodium sulfate, filtered and concentrated to yield a crude residue. This material was dissolved in 4 M HCl in dioxane (24 mL) and stirred for 3 hours. Evaporation of the solvent yielded (trans)-N,N,4-trimethyl-3-pyrrolidinamine in quantitative yield. LCMS: (M+H)+: 129.1.

Workup

  1. customto separate
  2. extractionThe aqueous phase was extracted with ether
  3. dry with materialthe combined organics were dried over sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customto yield a crude residue
  7. stirringstirred for 3 hours
  8. customEvaporation of the solvent

Sources & evidence

ORD record
ord-4abc4ce3477243c8bb8f7243b7760515
Source dataset
uspto-grants-2011_02
Patent number
US07893056B2

Reaction notes

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