Formaldehyde → HCID 67163859, compound

HRID 553043Notes

Reaction equation

HRID 553043 reaction equation
[CH2:1]([O:8][C:9]([N:11]1[CH2:17][C@H:16]2[C@H:13]([CH2:14][NH:15]2)[CH2:12]1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C=O.[C:20](O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>O>[CH2:1]([O:8][C:9]([N:11]1[CH2:17][C@H:16]2[C@H:13]([CH2:14][N:15]2[CH3:20])[CH2:12]1)=[O:10])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 712FormaldehydeHCID 5049666Sodium triacetoxyborohydrideHCID 23635040Phenylmethyl (1R,5R)-3,6-diazabicyclo[3.2.0]heptane-3-carboxylate

Product 1

HCID 67163859HCID 67163859, compoundYield 90.4%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a solution of (1R,5R)-3,6-diazabicyclo[3.2.0]heptane-3-carboxylic acid benzyl ester (14.2 g, 61.2 mmol; prepared according to patent WO 2001081347) and aqueous formaldehyde (38%, 100 mL, 1.38 mol; Fisher) in water (100 mL) was added sodium triacetoxyborohydride (25.8 g, 122 mmol; Aldrich). The mixture was stirred at room temperature until the reaction was complete according to HPLC analysis. The mixture was extracted with chloroform (3×100 mL) and the organic phase was washed with brine (100 mL) and concentrated under reduced pressure to afford the title compound (13.6 g, 55.3 mmol; 90% yield): 1H NMR (300 MHz, CD3OD) δ ppm 7.26-7.42 (5H, m), 5.15 (2H, s), 3.85 (1H, dd, J=7, 4 Hz), 3.69-3.79 (1H, m), 3.42-3.55 (1H, m), 3.13-3.25 (4H, m), 2.98-3.09 (1H, m), 2.32 (3H, s); MS (DCI/NH3) m/z 247 (M+H)+.

Workup

  1. extractionThe mixture was extracted with chloroform (3×100 mL)
  2. washthe organic phase was washed with brine (100 mL)
  3. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-7adea88d2fbd4d4a8b4a77d157ad9ec4
Source dataset
uspto-grants-2011_05
Patent number
US07951791B2

Reaction notes

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