Sodium Hydroxide → HCID 178511560, compound
Reaction equation
Cl.[NH2:2][C@H:3]1[CH2:8][CH2:7][C@H:6]([C:9](O)=[O:10])[CH2:5][CH2:4]1.COCCO[AlH2-]OCCOC.[Na+].[OH-].[Na+]>O>[NH2:2][C@H:3]1[CH2:8][CH2:7][C@H:6]([CH2:9][OH:10])[CH2:5][CH2:4]1Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Procedure
Trans-4-aminocyclohexane carboxylic acid hydrochloride (2.00 g, 14.3 mmol) was added in small portions to a stirred, hot (70-85° C.) solution of Red-Al (27.0 g) for 2 h (a semisolid formed), and heating was continued overnight. After 24 h, the reaction mixture was cooled to room temperature and treated with a solution of NaOH (3.8 g) in H2O (34 ml). Following the addition, the reaction was gradually heated to 80° C., and cooled. The toluene layer was separated and the aqueous layer was extracted with CHCl3 (3×100 ml). The organic layers were dried with MgSO4 and then concentrated under reduced pressure to provide the desired compound (1.81 g, 14.0 mmol) as a pure white solid in 50% yield. ES-MS: 130 (M+1).
Workup
- customformed), and
- temperatureheating
- waitAfter 24 h
- additionthe addition
- temperaturethe reaction was gradually heated to 80° C.
- temperaturecooled
- customThe toluene layer was separated
- extractionthe aqueous layer was extracted with CHCl3 (3×100 ml)
- dry with materialThe organic layers were dried with MgSO4
- concentrationconcentrated under reduced pressure
Sources & evidence
- ORD record
- ord-38406f2309af446ba70c468ffa9e86d6
- Source dataset
- uspto-grants-2015_11
- Patent number
- US09187479B2
Reaction notes
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