Hydrochloric Acid → HCID 14986524, compound

HRID 257221Notes

Reaction equation

HRID 257221 reaction equation
[CH3:1][C:2]1([CH3:12])[O:7][C:6]2[CH:8]=[CH:9][S:10][C:5]=2[C:4](=O)[CH2:3]1.[NH:13]1[CH2:17][CH2:16][CH2:15][CH2:14]1.C([BH3-])#N.[Na+].Cl>CO.O>[CH3:1][C:2]1([CH3:12])[O:7][C:6]2[CH:8]=[CH:9][S:10][C:5]=2[CH:4]([N:13]2[CH2:17][CH2:16][CH2:15][CH2:14]2)[CH2:3]1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 31268PyrrolidineHCID 5003444Sodium cyanoborohydride3×HCID 15643884129969-30-8

Product 1

HCID 14986524HCID 14986524, compoundYield 54%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

A solution of 5,6-dihydro-5,5-dimethylthieno[3,2-b]pyran-7-one (1.0 g, 5,5 mmol), pyrrolidine (2.3ml, 27.4(mmol) sodium cyanoborohydride (0.345 g, 5.5 mmol) and 1N aqueous hydrochloric acid (5.5ml, 5.5 mmol) in methanol (15ml) was stirred at rt for 1 day. Additional sodium cyanoborohydride (0.345 g, 5.5 mmol) was added and the solution was stirred an additional 1 day; additional sodium cyanoborohydride (1.0 g, 15.9 mmol) was added again and the mixture stirred 5 additional days. The mixture was poured into water (100 ml) and extracted with dichloromethane. The dichloromethane solution was washed with water and dried over sodium sulfate. The solvent was evaporated in vacuo and the residue was purified by medium pressure chromatography using 2% methanol in dichloromethane as the eluant to give the product 0.70 g (54%) as a yellow solid; mp 49°-50° C.; IR(KBr): 2971, 1560 and 1394 cm-1 ; MS:m/z 238 (MH+); 1H NMR (CDCl3): δ 1.27(s,3H), 1.45(s3H), 1.80(m,4H), 1.91(m,2H), 2.76(m,4H), 4.09(m,1H), 6.57(d,J=5.4 Hz,1H), and 7.04(d,J=5.4 Hz,1H).

Workup

  1. stirringthe mixture stirred 5 additional days
  2. extractionextracted with dichloromethane
  3. washThe dichloromethane solution was washed with water
  4. dry with materialdried over sodium sulfate
  5. customThe solvent was evaporated in vacuo
  6. customthe residue was purified by medium pressure chromatography

Sources & evidence

ORD record
ord-680b9b09f3a44e1a9ad01bac313baea3
Source dataset
uspto-grants-1993_11
Patent number
US05260453

Reaction notes

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