Methanol → (9H-fluoren-9-yl)methyl piperidine-1-carboxylate

HRID 1865793Notes

Reaction equation

HRID 1865793 reaction equation
C1C=CC(C(Cl)(C2C(Cl)=CC=CC=2)C2C=CC=CC=2)=CC=1.[C:22]([N:39]([CH2:47]COCCO)[CH2:40][C:41]1C=CC=[CH:43][CH:42]=1)([O:24][CH2:25][CH:26]1[C:38]2[C:33](=[CH:34][CH:35]=[CH:36][CH:37]=2)[C:32]2[C:27]1=[CH:28][CH:29]=[CH:30][CH:31]=2)=[O:23].N1C=CC=CC=1.CO>C1COCC1>[C:22]([N:39]1[CH2:40][CH2:41][CH2:42][CH2:43][CH2:47]1)([O:24][CH2:25][CH:26]1[C:27]2[C:32](=[CH:31][CH:30]=[CH:29][CH:28]=2)[C:33]2[C:38]1=[CH:37][CH:36]=[CH:35][CH:34]=2)=[O:23]

Participants

6

Reactant 4

HCID 887MethanolHCID 1049PyridineHCID 945242-Chlorotrityl chlorideHCID 57977485FmocN(Bn)CH2CH2OCH2CH2OH

Product 1

HCID 21896484(9H-fluoren-9-yl)methyl piperidine-1-carboxylate

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
65 °C

Procedure

THF (15 ml) was added to 2-Chlorotrityl chloride resin (4.0 g, 1.2 mmol/g) and the mixture was agitated for 25 min. FmocN(Bn)CH2CH2OCH2CH2OH (6.1 g, 14.7 mmol) in THF (25 ml) was added followed by pyridine (850 μl, 10.5 mmol) and the mixture was heated to 65° C. for 15 h. MeOH (5 ml) was added and heating was continued for 35 min. The resin was filtered, washed with DMF (3×), CH2Cl2 (3×). MeOH (3×) and Et2O (3×) to give 5.0 g. A small sample was dried carefully and deprotected with DCM/piperidine (1:1) for 30 min. Photometric determination of the resulting Fmoc-piperidine adduct (absorption at 301 nm) gave a resin loading of 0.45 mmol/g.

Workup

  1. temperatureheating
  2. waitwas continued for 35 min
  3. filtrationThe resin was filtered
  4. washwashed with DMF (3×), CH2Cl2 (3×)
  5. customMeOH (3×) and Et2O (3×) to give 5.0 g
  6. customA small sample was dried carefully
  7. waitdeprotected with DCM/piperidine (1:1) for 30 min

Sources & evidence

ORD record
ord-76012879e8d54af9b559a7f94df9ab73
Source dataset
uspto-grants-2009_12
Patent number
US07629318B2

Reaction notes

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