1-((tert-butoxy)carbonyl)-3-(((9H-fluoren-9-ylmethoxy)carbonyl)amino)piperidine-3-carboxylic acid → 3-Amino-1-(tert-butoxycarbonyl)piperidine-3-carboxylic acid
Reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH2:11][C:10]([NH:17]C(OCC2C3C=CC=CC=3C3C2=CC=CC=3)=O)([C:14]([OH:16])=[O:15])[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]>C(OC)(C)(C)C.C(O)(C)C>[NH2:17][C:10]1([C:14]([OH:16])=[O:15])[CH2:11][CH2:12][CH2:13][N:8]([C:6]([O:5][C:1]([CH3:2])([CH3:3])[CH3:4])=[O:7])[CH2:9]1Participants
3
Procedure
1-(tert-butoxycarbonyl)-3-{[(9H-fluoren-9-ylmethoxy)carbonyl]amino}piperidine-3-carboxylic acid was resolved by chiral HPLC resolution {Merck 50 mm 16 μm Kromasil Chirose 2 No. CT9014, tert-butylmethylether/iso-propanol (90/10). The second eluted enantiomer (800 mg, 1.71 mmol) 1-(tert-butoxycarbonyl)-3-{[(9H-fluoren-9-ylmethoxy)carbonyl]amino}piperidine-3-carboxylic acid (Isomer 2) was deprotected using an analogous procedure to that described for the equivalent step in Example 89 to give 3-amino-1-(tert-butoxycarbonyl)piperidine-3-carboxylic acid (Isomer 2); 1H NMR Spectrum: (D2O) 1.44 (s, 9H); 1.63 (m, 1H); 1.79 (d, 1H); 1.97 (d, 1H); 2.10 (m, 1H); 2.88 (t, 1H); 3.33 (d, 1H); 4.09 (m, 2H).
Sources & evidence
- ORD record
- ord-4a5c6d1708454ca7996e4920642ab21c
- Source dataset
- uspto-grants-2009_12
- Patent number
- US07632840B2
Reaction notes
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