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

HRID 1865790ノート

反応式

HRID 1865790 の反応式
[N:1]1([C:15]([O:17][CH2:18][CH:19]2[C:31]3[C:26](=[CH:27][CH:28]=[CH:29][CH:30]=3)[C:25]3[C:20]2=[CH:21][CH:22]=[CH:23][CH:24]=3)=[O:16])CC[CH:6]([C:9]2[CH:14]=[CH:13]C=CC=2)[C@H:2]1C(O)=O.C1C=CC(C(Cl)(C2C(Cl)=CC=CC=2)C2C=CC=CC=2)=CC=1.CCN(C(C)C)C(C)C.CO>C(Cl)Cl>[C:15]([N:1]1[CH2:13][CH2:14][CH2:9][CH2:6][CH2:2]1)([O:17][CH2:18][CH:19]1[C:31]2[C:26](=[CH:27][CH:28]=[CH:29][CH:30]=2)[C:25]2[C:20]1=[CH:21][CH:22]=[CH:23][CH:24]=2)=[O:16]

参加物

6

反応物 4

HCID 887MethanolHCID 81531Diisopropylethylamine2 回HCID 945242-Chlorotrityl chlorideHCID 131727814Fmoc-betaPhPro-OH

生成物 1

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

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

A solution of 7.4 g Fmoc-βPhPro-OH in 120 ml dry DCM was added to 12.0 g 2-chlorotrityl chloride resin (0.83 mmol/g, Novabiochem). DIPEA (3.0 ml) was added and the mixture was shaken for 10 min. Additional 4.5 ml DIPEA were added and shaking was continued for 145 min. Methanol (10 ml) was added the mixture was shaken for another 25 min. The resin was filtered off, washed with DCM (5×100 ml), methanol (2×100 ml) and DCM (4×100 ml). 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 0.54 mmol/g. The remaining resin was treated with 100 ml DCM and 80 ml piperidine at r.t. for 160 min, washed with DCM (10×100 ml) and diethyl ether (4×80 ml) and dried in vacuo to give 14.37 g HβPhPro-2-chlorotrityl resin.

後処理

  1. stirringshaking
  2. waitwas continued for 145 min
  3. stirringwas shaken for another 25 min
  4. filtrationThe resin was filtered off
  5. washwashed with DCM (5×100 ml), methanol (2×100 ml) and DCM (4×100 ml)
  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-3502538826284b2e9e8fe549380358a3
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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