Pyrrolidine → HCID 68620344, compound

HRID 1159428Notes

Reaction equation

HRID 1159428 reaction equation
[OH:1][C:2]1[C:9]([O:10][CH3:11])=[CH:8][C:5]([CH:6]=O)=[C:4]([O:12][CH3:13])[CH:3]=1.[NH:14]1[CH2:18][CH2:17][CH2:16][CH2:15]1.[BH-](OC(C)=O)(OC(C)=O)OC(C)=O.[Na+].OS([O-])(=O)=O.[Na+]>C(Cl)Cl.O>[CH3:11][O:10][C:9]1[CH:8]=[C:5]([CH2:6][N:14]2[CH2:18][CH2:17][CH2:16][CH2:15]2)[C:4]([O:12][CH3:13])=[CH:3][C:2]=1[OH:1]

Participants

7

Reactant 4

HCID 31268PyrrolidineHCID 516919Sodium BisulfateHCID 5049666Sodium triacetoxyborohydrideHCID 149209774-Hydroxy-2,5-dimethoxybenzaldehyde

Product 1

HCID 68620344HCID 68620344, compoundYield 58%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

Intermediate 58, 4-Hydroxy-2,5-dimethoxybenzaldehyde (1.2 g, 6.6 mmol) was added in portions for 30 min to a mixture of pyrrolidine (0.7 mL, 8.2 mmol) and NaB(OAc)3H (1.75 g, 8.2 mmol) in CH2Cl2 (20 mL) under vigorous stirring and cooling with an ice bath in an atmosphere of argon. The mixture was stirred for 12 h and cooled with an ice bath. Water (30 mL) and a 5 N solution of NaHSO4 were added to pH 1. The organic layer was separated and discarded. The aqueous one was alkalized with a saturated solution of K2CO3 to pH 6 and subjected to extraction with chloroform (2×50 mL). The combined extracts were dried with Na2SO4 and evaporated to give the title compound (0.9 g, 58%) as a yellow oil. LCMS data: 238.1 (M+H)+ and 168.0, 167.0 (M-pyrrolidine+H) (calculated for C15H23NO 237.3). 1H NMR data (DMSO-d6): 8.88 (br. s, 1H ArOH), 6.84 (s, 1H, Ar—H), 6.45 (s, 1H, Ar—H); 3.69 (s, 3H, —OCH3), 3.659 (s, 3H, —OCH3), 3.47 (s, 2H, —CH2—), 2.37-2.49 (m, 4H, pyrrolidine (CH2)2N), 1.60-1.73 (m, 4H, CH2CH2CH2CH2).

Workup

  1. temperaturecooling with an ice bath in an atmosphere of argon
  2. stirringThe mixture was stirred for 12 h
  3. temperaturecooled with an ice bath
  4. customThe organic layer was separated
  5. extractionsubjected to extraction with chloroform (2×50 mL)
  6. dry with materialThe combined extracts were dried with Na2SO4
  7. customevaporated

Sources & evidence

ORD record
ord-1740bd7e2fb1435d8ef87bdec9a7fc65
Source dataset
uspto-grants-2010_10
Patent number
US07812040B2

Reaction notes

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