Formaldehyde → HCID 137328992, compound

HRID 1879497Notes

Reaction equation

HRID 1879497 reaction equation
[C:1]([BH3-])#[N:2].[Na+].N[C:6]1[CH:7]=[C:8]([CH2:21][OH:22])[CH:9]=[C:10]([C:12]([CH3:20])([CH3:19])[O:13][SiH2:14][C:15]([CH3:18])([CH3:17])[CH3:16])[CH:11]=1.[CH2:23]=O>CO.[Cl-].[Zn+2].[Cl-]>[C:15]([SiH2:14][O:13][C:12]([CH3:20])([CH3:19])[C:10]1[CH:9]=[C:8]([CH2:21][OH:22])[CH:7]=[C:6]([N:2]([CH3:1])[CH3:23])[CH:11]=1)([CH3:18])([CH3:17])[CH3:16]

Participants

6

Reactant 3

HCID 712FormaldehydeHCID 5003444Sodium cyanoborohydrideHCID 137328990HCID 137328990, compound

Product 1

HCID 137328992HCID 137328992, compoundYield 82%

Reagents, catalysts & solvents 2

HCID 3007855ZincchlorideCatalystHCID 887MethanolSolvent2×

Procedure

Sodium cyanoborohydride (470 mg, 7.48 mmol) was added to a magnetically stirred solution of [3-amino-5-(tert-butyl-dimethyl-silanyloxymethyl)-phenyl]-methanol (1.0 g, 3.74 mmol) in methanol (30 mL). The reaction vessel was capped with a septum and pierced with a needle. In a separate flask, parafomaldehyde (449 mg, 15.0 mmol) was heated with heat gun and the gas cannulated into the reaction vessel with a stream of nitrogen. After all the paraformaldehyde was added, a solution of zinc chloride (510 mg, 3.74 mmol) in methanol (8 mL) was added dropwise. Gas evolution was observed. After the addition was complete, TLC indicated that the starting material had been consumed. The reaction mixture was diluted with ethyl acetate (100 mL) and washed with 1% aqueous ammonium hydroxide and then with brine. The solution was dried over sodium sulfate, filtered, concentrated, and purified by silica gel chromatography, eluting with 10-60% ethyl acetate/hexanes to give [3-(tert-butyl-dimethyl-silanyloxymethyl)-5-dimethylamino-phenyl]-methanol (906 mg, 82% yield) as a viscous oil.

Workup

  1. customThe reaction vessel was capped with a septum
  2. temperatureIn a separate flask, parafomaldehyde (449 mg, 15.0 mmol) was heated
  3. temperaturewith heat gun
  4. additionAfter the addition
  5. customhad been consumed
  6. additionThe reaction mixture was diluted with ethyl acetate (100 mL)
  7. washwashed with 1% aqueous ammonium hydroxide
  8. dry with materialThe solution was dried over sodium sulfate
  9. filtrationfiltered
  10. concentrationconcentrated
  11. custompurified by silica gel chromatography
  12. washeluting with 10-60% ethyl acetate/hexanes

Sources & evidence

ORD record
ord-17c37ee23b144356bda67b896d205498
Source dataset
uspto-grants-2012_11
Patent number
US08314250B2

Reaction notes

Loading…