Triethylamine → 2-[(Hexyloxy)carbonyl]-1-pyrrolidineheptanoic acid benzyl ester

HRID 1283843Notes

Reaction equation

HRID 1283843 reaction equation
[CH2:1]([O:7][C:8]([CH:10]1[CH2:14][CH2:13][CH2:12][NH:11]1)=[O:9])[CH2:2][CH2:3][CH2:4][CH2:5][CH3:6].I[CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][C:22]([O:24][CH2:25][C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1)=[O:23].C(N(CC)CC)C>C1C=CC=CC=1>[CH2:25]([O:24][C:22](=[O:23])[CH2:21][CH2:20][CH2:19][CH2:18][CH2:17][CH2:16][N:11]1[CH2:12][CH2:13][CH2:14][CH:10]1[C:8]([O:7][CH2:1][CH2:2][CH2:3][CH2:4][CH2:5][CH3:6])=[O:9])[C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 19991658HCID 19991658, compoundHCID 21516691Benzyl 7-iodoheptanoate

Product 1

HCID 537785812-[(Hexyloxy)carbonyl]-1-pyrrolidineheptanoic acid benzyl ester

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

A solution of 1.99 g. (0.01 mol.) of 2-[(hexyloxy)-carbonyl]pyrrolidine obtained in Example 1, 3.45 g. (0.01 mol.) of benzyl 7-iodoheptanoate and 1.21 g. (0.012 mol.) of triethylamine in 10 ml. of benzene is heated at 50° for 16 hours. The cooled reaction mixture is washed with 5% aqueous sodium bicarbonate, saturated aqueous chloride, dried, and concentrated in vacuo to give an oil, 2-[(hexyloxy)carbonyl]-1-pyrrolidineheptanoic acid benzyl ester.

Workup

  1. customThe cooled reaction mixture
  2. washis washed with 5% aqueous sodium bicarbonate, saturated aqueous chloride
  3. customdried
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-055e8ce77a9044ed9956beefbadf3e43
Source dataset
uspto-grants-1976_08
Patent number
US03976660

Reaction notes

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