HCID 20345020, compound → HCID 16641109, compound
Reaction equation
CN(C)C1CCCCC1NC(=O)OCC1C=CC=CC=1.[CH3:21][N:22]([CH3:39])[CH:23]1[CH2:28][CH2:27][CH2:26][CH2:25][CH:24]1[C:29]([O:31]CC1C=CC=CC=1)=[O:30]>>[CH3:21][N:22]([CH3:39])[C@H:23]1[CH2:28][CH2:27][CH2:26][CH2:25][C@H:24]1[C:29]([OH:31])=[O:30]Participants
Procedure
A mixture of the amino acid prepared in Part C (31.2 g., 0.15 mole), diphenyl phosphoryl azide (41.3 g.; 0.15 mole), and triethylamine (30.4 g., 0.30 mole) in 750 ml. benzene was refluxed with stirring for 1 hour. Benzyl alcohol (48.7 g., 0.45 mole) was added and the mixture refluxed overnight. The mixture was extracted with 10% HCl. The extract was washed with ether, made basic with 40% KOH, and extracted with ether. The organic layer was washed with water and saturated NaCl solution, dried, and evaporated. The residual oil was distilled to give 8.5 g. (20% yield) mixture of carbamate and benzyl ester, b.p. 130°-50°/0.1 mm. The nmr (CDCl3) was consistent with a mixture of benzyl N-(2-dimethylaminocyclohexyl)carbamate and benzyl 2-dimethylaminocyclohexanecarboxylate.
Sources & evidence
- ORD record
- ord-a22863e4a6184cc597714749bab295fb
- Source dataset
- uspto-grants-1979_04
- Patent number
- US04148914
Reaction notes
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