Chloroform-D → HCID 16641109, compound
Reaction equation
[2H]C(Cl)(Cl)Cl.[CH3:6][N:7]([CH3:24])[CH:8]1[CH2:13][CH2:12][CH2:11][CH2:10][CH:9]1[C:14]([O:16]CC1C=CC=CC=1)=[O:15]>>[CH3:6][N:7]([CH3:24])[C@H:8]1[CH2:13][CH2:12][CH2:11][CH2:10][C@H:9]1[C:14]([OH:16])=[O:15]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°/0.01 mm. The nmr (CDC13) was consistent with a mixture of benzyl N-(2-dimethylaminocyclohexyl) carbamate and benzyl 2-dimethylaminocyclohexanecarboxylate.
Sources & evidence
- ORD record
- ord-f842cd2424a44b07b5d05aedc58c6a89
- Source dataset
- uspto-grants-1980_07
- Patent number
- US04215114
Reaction notes
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