9-Fluorenylmethyl chloroformate → 4-Piperidinecarboxylic acid

HRID 376264Notes

Reaction equation

HRID 376264 reaction equation
C([N:18]1[CH2:23][CH2:22][C:21](C)([C:24]([OH:26])=[O:25])[CH2:20][CH2:19]1)(OCC1C2C(=CC=CC=2)C2C1=CC=CC=2)=O.C(Cl)(OCC1C2C(=CC=CC=2)C2C1=CC=CC=2)=O>>[NH:18]1[CH2:23][CH2:22][CH:21]([C:24]([OH:26])=[O:25])[CH2:20][CH2:19]1

Participants

3

Reactant 2

HCID 343679-Fluorenylmethyl chloroformateHCID 193618011-(9H-Fluoren-9-ylmethyl) 4-methyl-1,4-piperidinedicarboxylate

Product 1

HCID 37734-Piperidinecarboxylic acid

Procedure

Preparation of N-FMOC-4-methyl-4-piperidinecarboxylic acid was prepared as described in Step D of Preparation 2 utilizing the product of Step B as starting material, except as follows. After stirring the reaction mixture overnight in the presence of FMOCCl the mixture was concentrated in vacuo to remove dioxane. The aqueous phase was diluted with water and extracted with ether. The desired product was extracted into the ether phase (salt is soluble in ether). The combined ether and aqueous phase were acidified and extracted with ether. The combined ethereal phases were washed with brine, dried over MgSO4, filtered and concentrated in vacuo. The residue was purified by flash chromatography over silica gel eluting with 5%MeOH/CH2Cl2 to give the desired product. 1H-NMR (CDCl3, 400 Mhz):1.22 (s, 3H); 1.40 (bm, 2H); 2.02 (bs, 2H); 3.05 (bs,2H); 3.75 and 3.85 (bs, 1H); 4.21 (t, 1H); 4.41 (d, 2H) 7.29 (t, 2H); 7.38 (t, 2H); 7.55 (d, 2H); 7.75 (d, 2H).

Workup

  1. customwas prepared
  2. concentrationwas concentrated in vacuo
  3. customto remove dioxane
  4. additionThe aqueous phase was diluted with water
  5. extractionextracted with ether
  6. extractionThe desired product was extracted into the ether phase (salt is soluble in ether)
  7. extractionextracted with ether
  8. washThe combined ethereal phases were washed with brine
  9. dry with materialdried over MgSO4
  10. filtrationfiltered
  11. concentrationconcentrated in vacuo
  12. customThe residue was purified by flash chromatography over silica gel eluting with 5%MeOH/CH2Cl2

Sources & evidence

ORD record
ord-91bd5f26f2c142be927052f4a493d3ea
Source dataset
uspto-grants-2000_02
Patent number
US06020347

Reaction notes

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