9-Fluorenylmethyl chloroformate → HCID 71246275, compound

HRID 1486810Notes

Reaction equation

HRID 1486810 reaction equation
[CH:1]12[NH:17][CH:5]([CH:6]([C:8]3[CH:9]=[CH:10][C:11]([N:14]([CH3:16])[CH3:15])=[N:12][CH:13]=3)[CH2:7]1)[CH2:4][CH2:3][CH2:2]2.[C:18](Cl)([O:20][CH2:21][CH:22]1[C:34]2[C:29](=[CH:30][CH:31]=[CH:32][CH:33]=2)[C:28]2[C:23]1=[CH:24][CH:25]=[CH:26][CH:27]=2)=[O:19]>O1CCOCC1.C(=O)([O-])[O-].[Na+].[Na+]>[CH:33]1[C:34]2[CH:22]([CH2:21][O:20][C:18]([N:17]3[CH:5]4[CH:6]([C:8]5[CH:13]=[N:12][C:11]([N:14]([CH3:15])[CH3:16])=[CH:10][CH:9]=5)[CH2:7][CH:1]3[CH2:2][CH2:3][CH2:4]4)=[O:19])[C:23]3[C:28](=[CH:27][CH:26]=[CH:25][CH:24]=3)[C:29]=2[CH:30]=[CH:31][CH:32]=1

Participants

5

Reactant 2

HCID 343679-Fluorenylmethyl chloroformateHCID 71246677HCID 71246677, compound

Product 1

HCID 71246275HCID 71246275, compoundYield 98%

Reagents, catalysts & solvents 2

HCID 10340Sodium CarbonateSolventHCID 312751,4-DioxaneSolvent

Procedure

219 mg (0.95 mmol, 1 eq) of (−)-[5-(8-aza-bicyclo[3.2.1]oct-6-yl)-pyridine-2-yl]-dimethylamine (VII-1) are dissolved in 1.8 ml of dioxane and 2.75 ml of 10% sodium carbonate solution. 257 mg (1 mmol, 1.05 eq) of Fmoc-Cl in portions is added and it is stirred for 1 h at RT. After this time it is diluted with EE and washed with water. The aqueous phase is re-extracted for three times with EE. The combined organic phases are dried over sodium sulphate and the solvent is removed in vacuo. The crude product is purified by column chromatography (EE:hex=1:2). 422 mg (0.93 mmol, 98%) of a colorless foam/solid is obtained.

Workup

  1. additionAfter this time it is diluted with EE
  2. washwashed with water
  3. extractionThe aqueous phase is re-extracted for three times with EE
  4. dry with materialThe combined organic phases are dried over sodium sulphate
  5. customthe solvent is removed in vacuo
  6. customThe crude product is purified by column chromatography (EE:hex=1:2)

Sources & evidence

ORD record
ord-2422297ea9d74a8d9db0dc8f7f2372fc
Source dataset
uspto-grants-2016_08
Patent number
US09428497B2

Reaction notes

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