Triethylamine → 3-[[(1,1-Dimethylethoxy)carbonyl]amino]bicyclo[2.2.1]heptane-2-carboxylic acid
Reaction equation
[NH2:1][CH:2]1[CH:7]2[CH2:8][CH:4]([CH2:5][CH2:6]2)[CH:3]1[C:9]([OH:11])=[O:10].C(N(CC)CC)C.[C:19]([O:23][C:24](ON=C(C1C=CC=CC=1)C#N)=[O:25])([CH3:22])([CH3:21])[CH3:20]>O.O1CCOCC1>[C:19]([O:23][C:24]([NH:1][CH:2]1[CH:7]2[CH2:8][CH:4]([CH2:5][CH2:6]2)[CH:3]1[C:9]([OH:11])=[O:10])=[O:25])([CH3:22])([CH3:21])[CH3:20]Participants
6
Reactant 3
Product 1
Reagents, catalysts & solvents 2
Procedure
To a solution of 3-aminonorbornane-2-carboxylic acid (12.6 g.) in a mixture of water (100 ml.) and dioxane (100 ml.) were added triethylamine (12.2 g.) and 2-tert-butoxycarbonyloxyimino-2-phenylacetonitrile (16.2 g.). The mixture was stirred for 5 hours at ambient temperature and washed with ethyl acetate at pH 10 (each 250 ml., 2 times). The aqueous layer was adjusted to pH 2 with 10% aqueous hydrochloric acid. The acidified solution was extracted with ethyl acetate. The organic layer was dried over magnesium sulfate and filtered. The filtrate was evaporated to dryness under reduced pressure. The residue was pulverized with isopropyl ether to give 3-(N-tert-butoxycarbonylamino)norbornane-2-carboxylic acid (10.5 g.).
Workup
- washwashed with ethyl acetate at pH 10 (each 250 ml
- extractionThe acidified solution was extracted with ethyl acetate
- dry with materialThe organic layer was dried over magnesium sulfate
- filtrationfiltered
- customThe filtrate was evaporated to dryness under reduced pressure
Sources & evidence
- ORD record
- ord-be04438943f443529b1376add4e4c5c6
- Source dataset
- uspto-grants-1982_09
- Patent number
- US04349552
Reaction notes
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