Triethylamine → HCID 68577444, compound

HRID 1797269Notes

Reaction equation

HRID 1797269 reaction equation
[CH2:1]([O:8][C:9](=[O:23])[NH:10][C@H:11]([CH2:14][NH:15][C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])[CH2:12]I)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[F:24][C:25]1[CH:37]=[CH:36][C:28]([O:29][CH:30]2[CH2:35][CH2:34][NH:33][CH2:32][CH2:31]2)=[CH:27][CH:26]=1.C(N(CC)CC)C>ClCCl>[CH2:1]([O:8][C:9](=[O:23])[NH:10][C@H:11]([CH2:14][NH:15][C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])[CH2:12][N:33]1[CH2:32][CH2:31][CH:30]([O:29][C:28]2[CH:36]=[CH:37][C:25]([F:24])=[CH:26][CH:27]=2)[CH2:35][CH2:34]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 37348964-(4-Fluorophenoxy)piperidineHCID 68575959HCID 68575959, compound

Product 1

HCID 68577444HCID 68577444, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of [(R)-1-(tert-butoxycarbonylamino-methyl)-2-iodo-ethyl]-carbamic acid benzyl ester (0.61 g, 1.2 mmol) and 4-(4-fluoro-phenoxy)-piperidine (0.24 g, 1.23 mmol) in dichloromethane (5 ml) is treated with triethylamine (0.335 ml, 2.46 mmol). The reaction mixture is stirred at ambient temperature for 5 days, the solvent evaporated and the residue partitioned between ethylacetate and saturated aqueous NaHCO3. The ethylacetate phase is washed with brine, dried over MgSO4 and evaporated. The crude product is purified by flash silica chromatography (elution with 4:1 hexane/ethylacetate) to afford {(R)-1-(tert-butoxycarbonylamino-methyl)-2-[4-(4-fluoro-phenoxy)-piperidin-1-yl]-ethyl}-carbamic acid benzyl ester [MH]+ 502.2.

Workup

  1. customthe solvent evaporated
  2. customthe residue partitioned between ethylacetate and saturated aqueous NaHCO3
  3. washThe ethylacetate phase is washed with brine
  4. dry with materialdried over MgSO4
  5. customevaporated
  6. customThe crude product is purified by flash silica chromatography (elution with 4:1 hexane/ethylacetate)

Sources & evidence

ORD record
ord-09af756de638405a8c63bac6af954cce
Source dataset
uspto-grants-2006_04
Patent number
US07034042B2

Reaction notes

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