Iodine → 1-(2-Amino-1-(4-(benzyloxy)phenyl)ethyl)cyclohexanol
Reaction equation
[C:1]([CH:3]([C:11]1[CH:16]=[CH:15][C:14]([O:17][CH2:18][C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)=[CH:13][CH:12]=1)[C:4]1([OH:10])[CH2:9][CH2:8][CH2:7][CH2:6][CH2:5]1)#[N:2].[BH4-].[Na+].II>O1CCCC1>[NH2:2][CH2:1][CH:3]([C:4]1([OH:10])[CH2:9][CH2:8][CH2:7][CH2:6][CH2:5]1)[C:11]1[CH:12]=[CH:13][C:14]([O:17][CH2:18][C:19]2[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=2)=[CH:15][CH:16]=1Participants
5
Conditions
- Temperature
- 2.5 °C
Procedure
1-[Cyano(p-benzyloxyphenyl)methyl]cyclohexanol (50 g) was dissolved in tetrahydrofuran (300 ml) and sodium borohydride (30 g) was added at room temperature. Reaction mixture was cooled to 0-5° C. and charged with iodine solution drop wise (60 g) in 2.5 h. The reaction mass was stirred for 16 h at 25-30° C., filtered and washed with tetrahydrofuran (50 ml). The filtrate was cooled, DM water (500 ml) was added drop wise at 0-5° C. and tetrahydrofuran was distilled under reduced pressure at 40-45° C. to give residue. The residue was extracted with ethylacetate (250 ml×3), dried, concentrated, cooled and filtered to give 40 g (79.2%) of the 1-[2-amino-1-(4-benzyloxyphenyl)ethyl]-cyclohexanol.
Workup
- customReaction mixture
- filtrationfiltered
- washwashed with tetrahydrofuran (50 ml)
- temperatureThe filtrate was cooled
- additionDM water (500 ml) was added drop wise at 0-5° C.
- distillationtetrahydrofuran was distilled under reduced pressure at 40-45° C.
- customto give residue
- extractionThe residue was extracted with ethylacetate (250 ml×3)
- customdried
- concentrationconcentrated
- temperaturecooled
- filtrationfiltered
Sources & evidence
- ORD record
- ord-9818641b1fc040d08a5991934e2e7f73
- Source dataset
- uspto-grants-2012_11
- Patent number
- US08304578B2
Reaction notes
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