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

HRID 1865793노트

반응식

HRID 1865793 반응식
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]

참가 물질

6

반응물 4

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

생성물 1

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

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매2회

반응 조건

온도
65 °C

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-76012879e8d54af9b559a7f94df9ab73
출처 데이터셋
uspto-grants-2009_12
특허 번호
US07629318B2

반응 노트

불러오는 중…