Formaldehyde → HCID 67202473, compound

HRID 547584Notes

Reaction equation

HRID 547584 reaction equation
[CH2:1]=O.[CH2:3]([O:5][C:6]1[CH:11]=[CH:10][C:9]([N:12]2[C:21](=[O:22])[C:20]3[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=3)[N:14]=[C:13]2[C@H:23]2[CH2:28][NH:27][CH2:26][CH2:25][N:24]2[C:29](=[O:42])[CH2:30][C:31]2[CH:36]=[CH:35][C:34]([F:37])=[C:33]([C:38]([F:41])([F:40])[F:39])[CH:32]=2)=[CH:8][CH:7]=1)[CH3:4]>ClC(Cl)C.ClCCl>[CH2:3]([O:5][C:6]1[CH:11]=[CH:10][C:9]([N:12]2[C:21](=[O:22])[C:20]3[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=3)[N:14]=[C:13]2[C@H:23]2[CH2:28][N:27]([CH3:1])[CH2:26][CH2:25][N:24]2[C:29](=[O:42])[CH2:30][C:31]2[CH:36]=[CH:35][C:34]([F:37])=[C:33]([C:38]([F:41])([F:39])[F:40])[CH:32]=2)=[CH:8][CH:7]=1)[CH3:4]

Participants

5

Reactant 2

HCID 712FormaldehydeHCID 67201570HCID 67201570, compound

Product 1

HCID 67202473HCID 67202473, compoundYield 78.2%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 63651,1-DichloroethaneSolvent

Procedure

Formaldehyde (37% in water) (0.015 g, 0.18 mmol) was added to a solution of 20 (0.05 g, 0.09 mmol) in dichloroethane (5 mL), followed by Na(OAC)3BH (0.057 g, 0.27 mmol) at room temperature. The mixture was stirred overnight. The solution was diluted with dichloromethane, washed by saturated sodium bicarbonate, water, brine and dried over anhydrous sodium sulfate. The solvent was evaporated and the residue was purified by flash column to afford a white solid (40 mg). 1H NMR (CDCl3) 1.42 (t, 3H, J=7.0 Hz), 2.01-2.26 (m, 4H), 2.89 (m, 2H), 3.77 (m, 4H), 4.04 (q, 2H, J=7.0 Hz), 4.46 (m, 1H), 5.41 (m, 1H), 7.01 (m, 3H), 7.06 (m, 1H), 7.41 (m, 5H), 7.71 (m, 1H), 8.21 (d, 1H, J=8.08 Hz). MS (ESI+) 569.2 (MH+).

Workup

  1. washwashed by saturated sodium bicarbonate, water, brine
  2. dry with materialdried over anhydrous sodium sulfate
  3. customThe solvent was evaporated
  4. customthe residue was purified by flash column

Sources & evidence

ORD record
ord-0d86068d1007456a8229873b86cfbcf0
Source dataset
uspto-grants-2011_05
Patent number
US07939538B2

Reaction notes

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