NSC617625 → HCID 22560190, compound

HRID 983396Notes

Reaction equation

HRID 983396 reaction equation
[C:1]([CH:4]1[CH2:8][CH2:7][N:6]([CH2:9][C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)[CH2:5]1)(=[O:3])[CH3:2].[BH4-].[Na+]>CO>[CH2:9]([N:6]1[CH2:7][CH2:8][CH:4]([CH:1]([OH:3])[CH3:2])[CH2:5]1)[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1

Participants

4

Reactant 2

HCID 357952NSC617625HCID 4311764Sodium borohydride

Product 1

HCID 22560190HCID 22560190, compoundYield 74.6%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a 5° C. solution of 3-acetyl-1-benzylpyrrolidine (1 g, 4.9 mmol [L. E. Overman, J. Am. Chem. Soc. 1983, 105, 6622]) in methanol (10 mL) was added portionwise sodium borohydride (0.37 g, 9.8 mmol). After stirring at room temperature for 17 hours, the mixture was concentrated, diluted with ethyl acetate, washed with water, brine, dried with sodium sulfate and concentrated to afford the title compound (0.75 g). MSCI: m/z=206 (MH+).

Workup

  1. concentrationthe mixture was concentrated
  2. additiondiluted with ethyl acetate
  3. washwashed with water, brine
  4. dry with materialdried with sodium sulfate
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-8484d10411fa4e2f8592a0971fe058fc
Source dataset
uspto-grants-2005_03
Patent number
US06864259B2

Reaction notes

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