Formaldehyde → HCID 9798809, compound

HRID 2167084Notes

Reaction equation

HRID 2167084 reaction equation
[C:1]1([N:7]([CH:15]2[CH2:23][C:22]3[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=3)[CH2:16]2)[CH2:8][CH:9]2[CH2:14][CH2:13][CH2:12][CH2:11][NH:10]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C=O.[BH-](OC(C)=O)(OC(C)=O)O[C:28](C)=O.[Na+].[OH-].[Na+]>ClCCCl.C(Cl)Cl.C(O)(=O)C>[CH3:28][N:10]1[CH2:11][CH2:12][CH2:13][CH2:14][CH:9]1[CH2:8][N:7]([CH:15]1[CH2:23][C:22]2[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=2)[CH2:16]1)[C:1]1[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

8

Reactant 4

HCID 712FormaldehydeHCID 14798Sodium HydroxideHCID 5049666Sodium triacetoxyborohydrideHCID 9819448HCID 9819448, compound

Product 1

HCID 9798809HCID 9798809, compound

Reagents, catalysts & solvents 3

HCID 111,2-DichloroethaneSolventHCID 176Acetic AcidSolventHCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of compound 16 (0.2 g, 0.65 mmol) in DCE (10 mL) were added successively formaldehyde (35% in H2O, 0.08 mL, 0.98 mmol), Na(OAc)3BH (0.415 g, 1.95 mmol) and acetic acid (AcOH, 0.1 mL) at ice-cold conditions. The resulting mixture was allowed to stir at rt for 16 hours. The reaction mixture was diluted with DCM and basified with NaOH (1N). The organic layer was separated and washed with water and brine, dried over Na2SO4, filtered and concentrated. The crude material was purified by chromatography on 230-400 mesh silica gel eluting with 5% methanol-DCM to provide compound 17.

Workup

  1. customThe organic layer was separated
  2. washwashed with water and brine
  3. dry with materialdried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe crude material was purified by chromatography on 230-400 mesh silica gel eluting with 5% methanol-DCM

Sources & evidence

ORD record
ord-11671c1dcd89414aad79cfd9ad57fc49
Source dataset
uspto-grants-2015_06
Patent number
US09044482B2

Reaction notes

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