Sodium Hydroxide → HCID 68620132, compound

HRID 1159409Notes

Reaction equation

HRID 1159409 reaction equation
[BH-](OC(C)=O)(OC(C)=O)OC(C)=O.[Na+].[NH:15]1[CH2:19][CH2:18][CH2:17][CH2:16]1.[OH:20][C:21]1[CH:28]=[CH:27][C:24]([CH:25]=O)=[C:23]([O:29][CH3:30])[CH:22]=1.[OH-].[Na+]>C(Cl)Cl.O>[CH3:30][O:29][C:23]1[CH:22]=[C:21]([OH:20])[CH:28]=[CH:27][C:24]=1[CH2:25][N:15]1[CH2:19][CH2:18][CH2:17][CH2:16]1

Participants

7

Reactant 4

HCID 14798Sodium HydroxideHCID 31268PyrrolidineHCID 5195414-Hydroxy-2-MethoxybenzaldehydeHCID 5049666Sodium triacetoxyborohydride

Product 1

HCID 68620132HCID 68620132, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

NaB(OAc)3H (8.7 g, 0.041 mol) was added in portions for 30 min to a mixture of pyrrolidine (3.4 mL, 0.0.41 mol) and 4-hydroxy-2-methoxybenzaldehyde (5 g, 0.033 mol) in CH2Cl2 (50 mL) under vigorous stirring and cooling with an ice bath in an atmosphere of argon. The mixture was stirred for 2 h and cooled. Then 10 N NaOH (4.1 mL) and water (30 mL) were added. The organic layer was separated, the aqueous one was extracted with chloroform (2×50 mL). The organic fractions were evaporated. The residue was distributed between water and CH2Cl2. Concentrated HCl (2.98 mL) was added. The organic layer was separated and discarded. The aqueous one was alkalized with 10 N NaOH to pH 6 and extracted with chloroform (2×50 mL). The combined extracts were dried with Na2SO4, and evaporated to give the title compound (3.37 g, 07%) as yellow crystals. 1H-NMR (400 MHz)-data (dmso-d6, j, Hz): 9.25 (s, 1H ArOH), 7.02 (d, 1H, J=8.3, Ar—H), 6.36 (d, 1H, J=2.2, Ar—H) 6.30 (dd, 1H, J1=8.3, J2=2.2, Ar—H), 3.70 (s, 3H, ArOCH3), 3.44 (s, 2H, ArCH2), 2.38-2.44 (m, 4H, pyrrolidine (CH2)2N), 1.62-1.68 (m, 4H, CH2CH2CH2CH2).

Workup

  1. temperaturecooling with an ice bath in an atmosphere of argon
  2. stirringThe mixture was stirred for 2 h
  3. temperaturecooled
  4. customThe organic layer was separated
  5. extractionthe aqueous one was extracted with chloroform (2×50 mL)
  6. customThe organic fractions were evaporated
  7. additionConcentrated HCl (2.98 mL) was added
  8. customThe organic layer was separated
  9. extractionextracted with chloroform (2×50 mL)
  10. dry with materialThe combined extracts were dried with Na2SO4
  11. customevaporated

Sources & evidence

ORD record
ord-28e5d59187ff4991ae863ba56a159461
Source dataset
uspto-grants-2010_10
Patent number
US07812040B2

Reaction notes

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