Sodium Chloride → 7-dimethylamino-5-hydroxy-6,7,8,9-tetrahydro [5H] benzocycloheptene
Reaction equation
[BH4-].[Na+].[CH3:3][N:4]([CH3:17])[CH:5]1[CH2:11][CH2:10][C:9]2[CH:12]=[CH:13][CH:14]=[CH:15][C:8]=2[C:7](=[O:16])[CH2:6]1.[Cl-].[Na+]>O.C(O)C>[CH3:3][N:4]([CH3:17])[CH:5]1[CH2:11][CH2:10][C:9]2[CH:12]=[CH:13][CH:14]=[CH:15][C:8]=2[CH:7]([OH:16])[CH2:6]1Participants
6
Reactant 3
Product 1
Reagents, catalysts & solvents 2
Conditions
- Temperature
- 20 °C
Procedure
A solution of 8.7 g of sodium borohydride in 87 ml of water was added to a solution of 8.7 g of the product of Step A in 435 ml of ethanol and the mixture was stirred at 20° C for 11/2 hours and was then poured into ice water. The mixture was saturated with sodium chloride and was extracted with ethyl acetate. The organic phase was washed with aqueous sodium chloride solution, was dried and evaporated to dryness to obtain 8 g of raw 7-dimethylamino-5-hydroxy-6,7,8,9-tetrahydro [5H] benzocycloheptene which was used as is for the next step.
Workup
- extractionwas extracted with ethyl acetate
- washThe organic phase was washed with aqueous sodium chloride solution
- customwas dried
- customevaporated to dryness
Sources & evidence
- ORD record
- ord-0fa9f34a0f62490caf88cb36b997cfeb
- Source dataset
- uspto-grants-1978_05
- Patent number
- US04091115
Reaction notes
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