Hydrochloric Acid → HCID 70211045, compound

HRID 380476Notes

Reaction equation

HRID 380476 reaction equation
[C:1]1([C:11]([N:13]2[CH2:17][CH:16]([C:18]3[CH:22]=[CH:21][S:20][CH:19]=3)[CH:15]([C:23](OC)=[O:24])[CH2:14]2)=[O:12])[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][CH:2]=1.[Li+].[BH4-].C(Cl)Cl.Cl>C1COCC1>[C:1]1([C:11]([N:13]2[CH2:17][CH:16]([C:18]3[CH:22]=[CH:21][S:20][CH:19]=3)[CH:15]([CH2:23][OH:24])[CH2:14]2)=[O:12])[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][CH:2]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 6344DichloromethaneHCID 4148881Lithium borohydrideHCID 70214163HCID 70214163, compound

Product 1

HCID 70211045HCID 70211045, compoundYield 92.8%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of 0.48 g (1.31 mmol) of 1-(1-naphthoyl)-3-(SR)-carbomethoxy-4-(RS)-(3-thienyl)pyrrolidine and 2.6 mL (5.24 mmol) of LiBH4 (2M in THF) in 10 mL of THF was stirred at rt for 12 h. To the reaction mixture was added 50 mL of CH2Cl2 and 5 mL of 0.5N HCl. The fractions were partitioned and the aqueous fraction was extracted twice with CH2Cl2. The combined organic fractions were dried over Na2SO4, filtered and the filtrate was concentrated. The residue was purified by chomatography to give 0.41 g of the title compound. 1H NMR (CDCl3) δ3.45 (m, 2H), 7.47-7.90 (m, 8H);

Workup

  1. customThe fractions were partitioned
  2. extractionthe aqueous fraction was extracted twice with CH2Cl2
  3. dry with materialThe combined organic fractions were dried over Na2SO4
  4. filtrationfiltered
  5. concentrationthe filtrate was concentrated
  6. customThe residue was purified by chomatography

Sources & evidence

ORD record
ord-9ddf2794046048dbb1bb97a7e1220f52
Source dataset
uspto-grants-2001_10
Patent number
US06303593B1

Reaction notes

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