Piperidine → (9H-fluoren-9-yl)methyl piperidine-1-carboxylate
Reaction equation
[NH:1]1[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.N([C:16]([O:18][CH2:19][CH:20]1[C:32]2[C:27](=[CH:28][CH:29]=[CH:30][CH:31]=2)[C:26]2[C:21]1=[CH:22][CH:23]=[CH:24][CH:25]=2)=[O:17])[C@H](C=O)CCS(C)=O.C1C=CC2N(O)N=NC=2C=1.CC(C)N=C=NC(C)C>CN(C=O)C.CN(C1C=CN=CC=1)C>[C:16]([N:1]1[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1)([O:18][CH2:19][CH:20]1[C:21]2[C:26](=[CH:25][CH:24]=[CH:23][CH:22]=2)[C:27]2[C:32]1=[CH:31][CH:30]=[CH:29][CH:28]=2)=[O:17]Participants
Procedure
The resin was deprotected using a 20% solution of piperidine in DMF (1×3 min, 1×7 min, 20 ml each) and subsequently washed with DMF (1×20 ml). Acylation was carried out by addition of FmocMetOH (2.4 g, 3 eq), DMF (10 ml), HOBt (990 mg, 3 eq), and DIC (1.01 ml, 3 eq) and DMAP (260 mg, 0.1 eq). The coupling was left for 4 h and the resin was washed with DMF (7×20 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 0.43 m mol/g. The remaining resin was capped using a solution of acetic anhydride (2 M) and DMAP (0.1 M) in DMF (20 ml, 1×10 min) and subsequently washed with DMF (12×20 ml), methanol (3×40 ml) and diethyl ether (3×40 ml), and dried in vacuo to yield 3.9 g FmocMet-Rinkamide resin.
Workup
- washsubsequently washed with DMF (1×20 ml)
- washthe resin was washed with DMF (7×20 ml)
- customA small sample was dried carefully
- waitdeprotected with DCM/piperidine (1:1) for 30 min
Sources & evidence
- ORD record
- ord-d6c4ac5aff074b4cbf8c9c563fc22efc
- Source dataset
- uspto-grants-2009_12
- Patent number
- US07629318B2
Reaction notes
Loading…