2-Bromoethanol → cis(+/-)4-Azido-1-(2-hydroxyethyl)piperidin-3-ol
Reaction equation
[N:1]([C@H:4]1[CH2:9][CH2:8][NH:7][CH2:6][C@H:5]1[OH:10])=[N+:2]=[N-:3].C(N(CC)C(C)C)(C)C.Br[CH2:21][CH2:22][OH:23].C(OC(N[C@@H]1CCN(CCO)C[C@@H]1C(OC)=O)=O)C1C=CC=CC=1>>[N:1]([C@H:4]1[CH2:9][CH2:8][N:7]([CH2:21][CH2:22][OH:23])[CH2:6][C@H:5]1[OH:10])=[N+:2]=[N-:3]Participants
5
Procedure
Cis(±)4-azidopiperidin-3-ol (prepared following the procedure described in WO 2005/066176 for the chiral material) (0.945 g, 6.65 mmol), N,N-diisopropylethylamine (1.7 mL, 10 mmol) and 2-bromoethanol (0.61 mL, 8.64 mmol) were reacted as described for Intermediate 37, except heating for one hour. The solvent was removed under reduced pressure. The residue was taken up in dichloromethane (100 mL), washed with 1M sodium hydroxide solution (30 mL) and the aqueous phase was back extracted five times with dichloromethane (5×100 mL). The combined organic phases were dried over sodium sulfate. Chromatography on silica gel with dichloromethane/methanol 3:1 gave 1.15 g (93%) of the product as a colorless oil.
Workup
- customwere reacted
- temperatureexcept heating for one hour
- customThe solvent was removed under reduced pressure
- washwashed with 1M sodium hydroxide solution (30 mL)
- extractionthe aqueous phase was back extracted five times with dichloromethane (5×100 mL)
- dry with materialThe combined organic phases were dried over sodium sulfate
Sources & evidence
- ORD record
- ord-3b2d1dd513a54ba4bc96d518b3adddce
- Source dataset
- uspto-grants-2011_01
- Patent number
- US07875715B2
Reaction notes
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