Acetic Acid → HCID 11435798, compound

HRID 1431151Notes

Reaction equation

HRID 1431151 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-7aabce8752004efa918cd39bd12fbf46
Source dataset
uspto-grants-2015_01
Patent number
US08940741B2

Reaction notes

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