Acetic Acid → HCID 11435798, compound

HRID 449659Notes

Reaction equation

HRID 449659 reaction equation
[C@H:1]12[CH2:7][C@H:4]([NH:5][CH2:6]1)[CH2:3][N:2]2[C:8]([O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[O:9].C=O.[C:17](O)(=O)C.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>CO>[CH3:17][N:5]1[CH2:6][C@@H:1]2[CH2:7][C@H:4]1[CH2:3][N:2]2[C:8]([O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[O:9]

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 712FormaldehydeHCID 5049666Sodium triacetoxyborohydrideHCID 11521263(1S,4S)-2-Boc-2,5-diazabicyclo[2.2.1]heptane

Product 1

HCID 11435798HCID 11435798, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

(1S,4S)-tert-Butyl 2,5-diazabicyclo[2.2.1]heptane-2-carboxylate (2.5 g, 12.6 mmol, Eq: 1.00) was dissolved in 126 ml of methanol. Formaldehyde (23.5 ml of a 37% aqueous solution) and acetic acid (2.17 ml) were added. Sodium triacetoxyborohydride (4.01 g, 18.9 mmol, Eq: 1.50) was added in portions. The reaction was stirred at room temperature overnight. The reaction was concentrated on a rotary evaporator. DCM and sodium bicarbonate were added to the residue and the layers were separated. The organic layer was washed with dilute bicarbonate, concentrated, and used without further purification.

Workup

  1. concentrationThe reaction was concentrated on a rotary evaporator
  2. additionDCM and sodium bicarbonate were added to the residue
  3. customthe layers were separated
  4. washThe organic layer was washed with dilute bicarbonate
  5. concentrationconcentrated
  6. customused without further purification

Sources & evidence

ORD record
ord-858952c1ba3445b4877990a2bd941f38
Source dataset
uspto-grants-2013_07
Patent number
US08481540B2

Reaction notes

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