Hydrochloric Acid → HCID 68620809, compound

HRID 1159424Notes

Reaction equation

HRID 1159424 reaction equation
[BH-](O[C:11]([CH3:13])=[O:12])(OC(C)=O)OC(C)=O.[Na+].[NH:15]1[CH2:19][CH2:18][CH2:17][CH2:16]1.[CH3:20][C:21]1[CH:28]=C(O)[CH:26]=[CH:25][C:22]=1C=O.Cl>C(Cl)Cl>[CH3:26][C:25]1[CH:22]=[C:21]([CH2:28][N:15]2[CH2:19][CH2:18][CH2:17][CH2:16]2)[CH:20]=[CH:13][C:11]=1[OH:12]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 31268PyrrolidineHCID 4581854-Hydroxy-2-methylbenzaldehydeHCID 5049666Sodium triacetoxyborohydride

Product 1

HCID 68620809HCID 68620809, compoundYield 86%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

NaB(OAc)3H (11.8 g, 0.056 mol) was added in portions for 15 min to a mixture of pyrrolidine (3.3 mL, 0.041 mol) and 2-methyl-4-hydroxybenzaldehyde (5 g, 0.037 mol) in CH2Cl2 (100 mL) under vigorous stirring and cooling with an ice bath in an atmosphere of argon Ar. The mixture was stirred for 20 h and cooled with an ice bath. Concentrated HCl (10 mL) was added. The organic layer was separated and discarded. The aqueous one was alkalized with K2CO3 to pH 9 (30 mL) and extracted with EtOAc (4×100 mL). The combined extracts were dried with Na2SO4, and evaporated to give the title compound (6.06 g, 86%) was obtained as white crystals. H-NMR (400 MHz)-data (DMSO-d6, J, Hz): 9.18 (br s, 1H, OH); 6.83 (s, 2H, ArH); 3.79 (s, 3H, CH3); 3.44 (s, 2H, CH2Ar); 2.36-2.44 (m, 4H, CH2CH2CH2CH2,); 1.65-1.72 (m, 4H, CH2CH2CH2CH2).

Workup

  1. temperaturecooling with an ice bath in an atmosphere of argon Ar
  2. stirringThe mixture was stirred for 20 h
  3. temperaturecooled with an ice bath
  4. customThe organic layer was separated
  5. extractionextracted with EtOAc (4×100 mL)
  6. dry with materialThe combined extracts were dried with Na2SO4
  7. customevaporated

Sources & evidence

ORD record
ord-e8c7d09c96e246e4bc1c42de5e21cc6b
Source dataset
uspto-grants-2010_10
Patent number
US07812040B2

Reaction notes

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