Triethylamine → HCID 117697335, compound

HRID 1778474Notes

Reaction equation

HRID 1778474 reaction equation
[CH3:1][O:2][C:3](=[O:14])[CH2:4][CH:5]1[CH2:12][CH:11]2[NH:13][CH:7]([CH2:8][O:9][CH2:10]2)[CH2:6]1.C(N(CC)CC)C.Cl[C:23]([O:25][CH2:26][C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1)=[O:24]>ClCCl>[CH2:26]([O:25][C:23]([N:13]1[CH:7]2[CH2:6][CH:5]([CH2:4][C:3]([O:2][CH3:1])=[O:14])[CH2:12][CH:11]1[CH2:10][O:9][CH2:8]2)=[O:24])[C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 10387Benzyl chloroformateHCID 117698048HCID 117698048, compound

Product 1

HCID 117697335HCID 117697335, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of (3-oxa-9-aza-bicyclo[3.3.1]non-7-yl)-acetic acid methyl ester (Compound AG) (179 mg, 0.90 mmol) in 10 mL of dichloromethane was added triethylamine (0.5 mL, 3.6 mmol). The mixture was stirred at room temperature for 15 mins and then benzyl chloroformate (0.25 mL, 1.8 mmol) was added dropwise at 0° C. After the reaction mixture was stirred at room temperature for 2 hours, it was concentrated in vacuo. The residue was purified by flash column chromatography to afford 7-methoxycarbonylmethyl-3-oxa-9-aza-bicyclo[3.3.1]nonane-9-carboxylic acid benzyl ester as colorless oil (Compound AI) (0.13 g, 44%) MS: calc'd (MH+) 334, measured (MH+) 334.

Workup

  1. stirringAfter the reaction mixture was stirred at room temperature for 2 hours
  2. concentrationit was concentrated in vacuo
  3. customThe residue was purified by flash column chromatography

Sources & evidence

ORD record
ord-f550984348224ac68f3ddb9e439eb52b
Source dataset
uspto-grants-2016_02
Patent number
US09266904B2

Reaction notes

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