Hydrochloric Acid → HCID 68619468, compound

HRID 1159415Notes

Reaction equation

HRID 1159415 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[C:30]2[C:25](=[CH:26][CH:27]=[CH:28][CH:29]=2)[C:24]([CH:31]=O)=[CH:23][CH:22]=1.Cl>CCOCC>[N:15]1([CH2:31][C:24]2[C:25]3[C:30](=[CH:29][CH:28]=[CH:27][CH:26]=3)[C:21]([OH:20])=[CH:22][CH:23]=2)[CH2:19][CH2:18][CH2:17][CH2:16]1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 31268PyrrolidineHCID 3442904-Hydroxy-1-naphthaldehydeHCID 5049666Sodium triacetoxyborohydride

Product 1

HCID 68619468HCID 68619468, compoundYield 112.2%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

NaB(OAc)3H (6.4 g, 0.030 mol) was added in portions for 15 min to a mixture of pyrrolidine (2.1 mL, 0.025 mol) and 4-hydroxynaphthalene-1-carbaldehyde (3.40 g, 0.020 mol) in (C2H5)2O (80 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 (2×100 mL) (C2H5)2O. The combined extracts were dried with Na2SO4, and evaporated to give the title compound (5.1 g, 75%) was obtained as white crystals. LCMS-data: 228.1 and 229.1 (M+H)+, (calculated for C15H17NO 227.13). 1H 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 (2×100 mL) (C2H5)2O
  6. dry with materialThe combined extracts were dried with Na2SO4
  7. customevaporated

Sources & evidence

ORD record
ord-b92cf99a4f4449eab5d64de20a9f8c24
Source dataset
uspto-grants-2010_10
Patent number
US07812040B2

Reaction notes

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