Formaldehyde → HCID 71239200, compound

HRID 1842710Notes

Reaction equation

HRID 1842710 reaction equation
C=O.[CH2:3](N(CC)CC)C.Cl.Cl.[CH2:12]([N:19]1[CH2:22][C:21]2([CH2:26][CH2:25][CH2:24][NH:23]2)[CH2:20]1)[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>ClCCCl>[CH2:12]([N:19]1[CH2:22][C:21]2([CH2:26][CH2:25][CH2:24][N:23]2[CH3:3])[CH2:20]1)[C:13]1[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=1

Participants

6

Reactant 4

HCID 712FormaldehydeHCID 8471TriethylamineHCID 5049666Sodium triacetoxyborohydrideHCID 509990282-Benzyl-2,5-diazaspiro[3.4]octane--hydrogen chloride (1/2)2×

Product 1

HCID 71239200HCID 71239200, compoundYield 100%

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Conditions

Temperature
10 °C

Procedure

Paraformaldehyde (70.91 g, 787 mmol) and triethylamine (119.5 g, 1.18 mol) were added to a mixture of 2-benzyl-2,5-diazaspiro[3.4]octane dihydrochloride (Intermediate 49, 65 g, 236.2 mmol) in 1,2-dichloroethane (700 mL) and the mixture was stirred for 1 h at 10° C. Sodium triacetoxyborohydride (110.8 g, 1.18 mol) was then added and the mixture was stirred for 12 h at 15° C. The mixture was then filtered and the filter cake was washed with CH2Cl2 (3×500 mL). The combined organic solutions were washed with brine (500 mL), dried (MgSO4) and concentrated in vacuo to give the title compound (51.1 g, 94%) as yellow oil; 1H NMR: (300 MHz, CDCl3) 1.75 (2H, m), 2.16 (2H, m), 2.49 (3H, s), 2.64 (2H, d), 3.10 (2H, d), 3.28 (2H, d), 3.66 (2H, s), 7.22-7.62 (5H, m).

Workup

  1. stirringthe mixture was stirred for 12 h at 15° C
  2. filtrationThe mixture was then filtered
  3. washthe filter cake was washed with CH2Cl2 (3×500 mL)
  4. washThe combined organic solutions were washed with brine (500 mL)
  5. dry with materialdried (MgSO4)
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-fb01bcb10aea4ccb9b668acd2b67c08a
Source dataset
uspto-grants-2015_02
Patent number
US08946235B2

Reaction notes

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