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

HRID 1865793ノート

反応式

HRID 1865793 の反応式
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]

参加物

6

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒2 回

反応条件

温度
65 °C

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-76012879e8d54af9b559a7f94df9ab73
出典データセット
uspto-grants-2009_12
特許番号
US07629318B2

反応ノート

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