Hydrochloric Acid → HCID 22720210, compound

HRID 1159420Notes

Reaction equation

HRID 1159420 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.[CH3:20][O:21][C:22]1[C:29]([OH:30])=[CH:28][C:25]([CH:26]=O)=[CH:24][CH:23]=1.Cl>C(Cl)Cl>[CH3:20][O:21][C:22]1[CH:23]=[CH:24][C:25]([CH2:26][N:15]2[CH2:19][CH2:18][CH2:17][CH2:16]2)=[CH:28][C:29]=1[OH:30]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 12127IsovanillinHCID 31268PyrrolidineHCID 5049666Sodium triacetoxyborohydride

Product 1

HCID 22720210HCID 22720210, compoundYield 85%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

NaB(OAc)3H (32 g, 0.15 mol) was added in portions for 15 min to a mixture of pyrrolidine (9.1 mL, 0.11 mol) and 4-methoxy-5-hydroxybenzaldehyde (15.2 g, 0.1 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 (21 mL) was added. The organic layer was separated and discarded. The aqueous one was alkalized with K2CO3 to pH 9 (60 mL) and extracted with chloroform (3×100 mL). The combined extracts were dried with Na2SO4, and evaporated to give the title compounds (17.6 g, 85%) as white crystals. LCMS-data: 208.1 and 209.1 (M+H)+, (calculated for C12H17NO2 207.1). 1H NMR (400 MHz)-data (DMSO-d6, J, Hz): 8.81 (br s, 1H, OH); 6.80 (d, 1H, ArH, J=8.3 Hz); 6.73 (d, 1H, ArH, J=2 Hz); 6.65 (dd, 1H, ArH, J1=2 Hz, J2=8 Hz); 3.72 (s, 3H, OCH3); 3.40 (s, 2H, CH2Ar); 2.41-2.33 (m, 4H, CH2CH2CH2CH2); 1.70-1.62 (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 chloroform (3×100 mL)
  6. dry with materialThe combined extracts were dried with Na2SO4
  7. customevaporated

Sources & evidence

ORD record
ord-bf739f55178b47e280c5d28045a19bec
Source dataset
uspto-grants-2010_10
Patent number
US07812040B2

Reaction notes

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