Acetic Acid → HCID 86585236, compound

HRID 1699967Notes

Reaction equation

HRID 1699967 reaction equation
[CH3:1][O:2][C:3]([N:5]1[CH2:9][CH:8]([C:10]2[CH:15]=[CH:14][C:13]([O:16][CH3:17])=[C:12]([O:18][CH:19]3[CH2:23][CH2:22][CH2:21][CH2:20]3)[CH:11]=2)[C@:7]([C:25](=O)[CH3:26])([CH3:24])[CH2:6]1)=[O:4].C(O)(=O)C.[CH3:32][NH:33][NH2:34]>CO>[CH3:1][O:2][C:3]([N:5]1[CH2:9][CH:8]([C:10]2[CH:15]=[CH:14][C:13]([O:16][CH3:17])=[C:12]([O:18][CH:19]3[CH2:23][CH2:22][CH2:21][CH2:20]3)[CH:11]=2)[C@@:7]([CH3:24])([C:25](=[N:34][NH:33][CH3:32])[CH3:26])[CH2:6]1)=[O:4]

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 6061Methylhydrazine2×HCID 12019362HCID 12019362, compound2×

Product 1

HCID 86585236HCID 86585236, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a stirred solution of (R)-3-acetyl-4-(3-cyclopentyloxy-4-methoxyphenyl)-3-methyl-pyrrolidine-1-carboxylic acid methyl ester (see Example 12 of Feldman et al. U.S. Pat. No. 5,665,654, incorporated herein by reference) (or (R)-3-acetyl-4-(3-cyclopentyloxy-4-methoxyphenyl)-3-methyl-pyrrolidine-1-carboxylic acid methyl ester) (0.133 mmol, 50 mg) in methanol (2 mL) with catalytic amount of acetic acid (20 μL) was added methyl hydrazine (0.147 mmol, 7.8 μL). The reaction was heated gently for 36 hours, and three more portions of methl hydrazine were added. The resulting hydrazone was purified by HPLC. The named product was confirmed by HNMR.

Workup

  1. temperatureThe reaction was heated gently for 36 hours
  2. customThe resulting hydrazone was purified by HPLC

Sources & evidence

ORD record
ord-03bc68a607f6469f80bf3b13853c3361
Source dataset
uspto-grants-2002_02
Patent number
US06348602B1

Reaction notes

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