Hydrochloric Acid → HCID 57698768, compound

HRID 1159413Notes

Reaction equation

HRID 1159413 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.Cl[C:21]1[CH:22]=[C:23]([CH:26]=[CH:27][C:28]=1[OH:29])[CH:24]=O.[ClH:30]>C(Cl)Cl>[Cl:30][C:22]1[CH:21]=[C:28]([OH:29])[CH:27]=[CH:26][C:23]=1[CH2:24][N:15]1[CH2:19][CH2:18][CH2:17][CH2:16]1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 170223-Chloro-4-hydroxybenzaldehydeHCID 31268PyrrolidineHCID 5049666Sodium triacetoxyborohydride

Product 1

HCID 57698768HCID 57698768, compoundYield 52%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

NaB(OAc)3H (20 g, 0.094 mol) was added in portions for 15 min to a mixture of pyrrolidine (7.78 mL, 0.11 mol) and 3-chloro-4-hydroxybenzaldehyde (12.5 g, 0.079 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 (18 mL) was added. The organic layer was separated and discarded. The aqueous one was alkalized with 10 N NaOH to pH 9 (30 mL) and extracted with chloroform (3×100 mL). The combined extracts were dried with Na2SO4, and evaporated. The residue was purified by chromatography (silica gel 63-100μ, 8 mL, CHCl3/5% i-PrOH to give the title compound (8.07 g, 52%) was obtained as white crystals. LCMS-data: 212 and 214 (M+H)+, (calculated for C11H14NOCl 211.6); 1H NMR (400Mz)-data (DMSO-d6, J, Hz): 9.95 (br s, 1H, OH); 7.20 (d, 1H, Ar, J=2 Hz); 7.00 (dd, 1H, Ar, J1=2 Hz, J2=8.1 Hz); 6.89 (d, 1H, Ar, J=8.1); 3.43 (s, 2H, CH2); 2.35-2.40 (m, 4H); 1.63-1.69 (m, 4H).

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 chloroform (3×100 mL)
  6. dry with materialThe combined extracts were dried with Na2SO4
  7. customevaporated
  8. customThe residue was purified by chromatography (silica gel 63-100μ, 8 mL, CHCl3/5% i-PrOH

Sources & evidence

ORD record
ord-98aaa6f5ab3f42d78533e2bf133416df
Source dataset
uspto-grants-2010_10
Patent number
US07812040B2

Reaction notes

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