Decylamine → HCID 66761243, compound

HRID 561810Notes

Reaction equation

HRID 561810 reaction equation
[Si:1]([O:8][CH2:9][C:10]1[CH:11]=[C:12]([CH:15]=[CH:16][C:17]=1[Cl:18])[CH:13]=[O:14])([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].CCCCCCCCCCN.[BH4-].[Na+]>CO>[Si:1]([O:8][CH2:9][C:10]1[CH:11]=[C:12]([CH2:13][OH:14])[CH:15]=[CH:16][C:17]=1[Cl:18])([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2]

Participants

5

Reactant 3

HCID 8916DecylamineHCID 4311764Sodium borohydrideHCID 86635911HCID 86635911, compound

Product 1

HCID 66761243HCID 66761243, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 3-({[tert-butyl(dimethyl)silyl]oxy}methyl)-4-chlorobenzaldehyde from step 3 of Amine 10 synthesis (1 eq.) in methanol (0.14 M) was added sodium borohydride (5 eq.). The resulting mixture was stirred at RT 3 h. The reaction was quenched by the addition of sat. aq. NH4Cl and then extracted with EtOAc. The combined organic extracts were washed with sat. aq. NaHCO3, dried over MgSO4 and filtered. Concentration of the filtrate in vacuo afforded an colorless oil. Purification of the crude product thus obtained by way of flash chromatography (SiO2, Hex→1:1 (v/v) Hex:EtOAc) afforded the title compound.

Workup

  1. customThe reaction was quenched by the addition of sat. aq. NH4Cl
  2. extractionextracted with EtOAc
  3. washThe combined organic extracts were washed with sat. aq. NaHCO3
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. customConcentration of the filtrate in vacuo afforded an colorless oil
  7. customPurification of the crude product
  8. customthus obtained by way of flash chromatography (SiO2, Hex→1:1 (v/v) Hex:EtOAc)

Sources & evidence

ORD record
ord-eef68dd42c8946988f719e1cc2538468
Source dataset
uspto-grants-2011_11
Patent number
US08063105B2

Reaction notes

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