Diisopropylethylamine → tert-Butyl 2-[(3-(methylcarbamoyl)isoxazol-5-ylmethoxycarbonylamino)methyl]-6-azaspiro[3.4]octane-6-carboxylate
Reaction equation
[NH2:1][CH2:2][CH:3]1[CH2:6][C:5]2([CH2:10][CH2:9][N:8]([C:11]([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:12])[CH2:7]2)[CH2:4]1.[C:18](=O)([O:30]C1C=CC([N+]([O-])=O)=CC=1)[O:19][CH2:20][C:21]1[O:25][N:24]=[C:23]([C:26](=[O:29])[NH:27][CH3:28])[CH:22]=1.C(N(CC)C(C)C)(C)C>>[CH3:28][NH:27][C:26]([C:23]1[CH:22]=[C:21]([CH2:20][O:19][C:18]([NH:1][CH2:2][CH:3]2[CH2:4][C:5]3([CH2:10][CH2:9][N:8]([C:11]([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:12])[CH2:7]3)[CH2:6]2)=[O:30])[O:25][N:24]=1)=[O:29]Participants
4
Reactant 3
Product 1
Procedure
The process is performed according to the procedure described in Example 1, step 1.1. Starting with 0.24 g (1.00 mmol) of tert-butyl 2-aminomethyl-6-azaspiro[3.4]octane-6-carboxylate (isomer 2b), described in Example 9 (step 9.1.), 0.321 g (1.00 mmol) of 3-(methylcarbamoyl)isoxazol-5-ylmethyl 4-nitrophenyl carbonate, obtained in step 4.1., 0.258 g (2.00 mmol) of N,N-diisopropylethylamine and 0.012 g (0.10 mmol) of N,N-dimethylaminopyridine, and after purification by chromatography on silica gel, eluting with a 98/2 mixture of dichloromethane and methanol, 0.320 g of pure product is thus obtained in the form of an amorphous solid.
Workup
- customobtained in step 4.1
- washeluting with a 98/2 mixture of dichloromethane and methanol, 0.320 g of pure product
- customis thus obtained in the form of an amorphous solid
Sources & evidence
- ORD record
- ord-877dbab36b05420391b83f872007122a
- Source dataset
- uspto-grants-2014_11
- Patent number
- US08889702B2
Reaction notes
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