Ammonium Acetate → 4-Amino-1-[2-(6-methoxy-quinazolin-4-yl)-ethyl]-cyclohexanol
Reaction equation
C([O-])(=O)C.[NH4+:5].C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].[OH:20][C:21]1([CH2:28][CH2:29][C:30]2[C:39]3[C:34](=[CH:35][CH:36]=[C:37]([O:40][CH3:41])[CH:38]=3)[N:33]=[CH:32][N:31]=2)[CH2:26][CH2:25][C:24](=O)[CH2:23][CH2:22]1>CO>[NH2:5][CH:24]1[CH2:25][CH2:26][C:21]([CH2:28][CH2:29][C:30]2[C:39]3[C:34](=[CH:35][CH:36]=[C:37]([O:40][CH3:41])[CH:38]=3)[N:33]=[CH:32][N:31]=2)([OH:20])[CH2:22][CH2:23]1Participants
5
Procedure
Ammonium acetate (14 g, 44 mmol) and sodium triacetoxyborohydride (1.2 g, 5 mmol) were added to a solution of 4-hydroxy-4-[2-(6-methoxy-quinazolin-4-yl)-ethyl]-cyclohexanone (1.25 g, 4.2 mmol) in methanol (50 ml). The reaction mixture was stirred overnight and concentrated to dryness by rotary evaporation. The residue was diluted with water (100 ml) and dichloromethane (100 ml), the phases were separated and the aqueous phase was extracted twice using 50 ml of dichloromethane each time. The combined organic phases were dried over Na2SO4, filtered and concentrated to dryness by rotary evaporation.
Workup
- concentrationconcentrated to dryness by rotary evaporation
- additionThe residue was diluted with water (100 ml) and dichloromethane (100 ml)
- customthe phases were separated
- extractionthe aqueous phase was extracted twice
- dry with materialThe combined organic phases were dried over Na2SO4
- filtrationfiltered
- concentrationconcentrated to dryness by rotary evaporation
Sources & evidence
- ORD record
- ord-9613ea9612c14e66979c1bfb552c9615
- Source dataset
- uspto-grants-2007_05
- Patent number
- US07223776B2
Reaction notes
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