Triethylamine → HCID 69414529, compound

HRID 1827150Notes

Reaction equation

HRID 1827150 reaction equation
[C:1]([C:8]1([OH:16])[CH2:13][CH2:12][N:11](CN)[CH2:10][CH2:9]1)([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2].[C:17](Cl)([O:19][CH2:20][C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)=[O:18].[CH2:28]([N:30](CC)CC)C>C(Cl)Cl>[C:1]([C:8]1([OH:16])[CH2:9][CH2:10][N:11]([C:17]([O:19][CH2:20][C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)=[O:18])[CH:12]([CH2:28][NH2:30])[CH2:13]1)([O:3][C:4]([CH3:5])([CH3:6])[CH3:7])=[O:2]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 10387Benzyl chloroformateHCID 69414377HCID 69414377, compound

Product 1

HCID 69414529HCID 69414529, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

To a cooled (0° C.), stirred solution of 4-BOC-aminomethyl-piperidin-4-ol (0.35 g, 1.52 mmol) in dried CH2Cl2 (5 mL), under N2 was slowly added CBZ-Cl (0.24 mL, 1.67 mmol), followed by triethylamine (0.42 mL, 3.04 mmol). The ice bath was removed and the reaction solution was stirred to rt in 1 h, then concentrated in vacuo. The residue was purified by silica gel chromatography (10 CH2Cl2:1-20 IPA:89-10 hexane)) to give 4-BOC-aminomethyl-1-CBZ-piperidin-4-ol. M.S.(M+1):365.39

Workup

  1. customThe ice bath was removed
  2. concentrationconcentrated in vacuo
  3. customThe residue was purified by silica gel chromatography (10 CH2Cl2:1-20 IPA:89-10 hexane))

Sources & evidence

ORD record
ord-04029cda5ff94137a29e0144e9400f8c
Source dataset
uspto-grants-2006_05
Patent number
US07053089B2

Reaction notes

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