Triethylamine → (R)-3-((S)-1-hydroxy-5-methoxy-1-phenylpentyl)piperidine-1-carbonyl chloride
Reaction equation
[CH3:1][O:2][CH2:3][CH2:4][CH2:5][CH2:6][C@@:7]([C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)([C@@H:9]1[CH2:14][CH2:13][CH2:12][NH:11][CH2:10]1)[OH:8].C(N(CC)CC)C.[Cl:28][C:29](Cl)([O:31]C(=O)OC(Cl)(Cl)Cl)Cl>C(Cl)Cl>[OH:8][C@@:7]([C@@H:9]1[CH2:14][CH2:13][CH2:12][N:11]([C:29]([Cl:28])=[O:31])[CH2:10]1)([C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)[CH2:6][CH2:5][CH2:4][CH2:3][O:2][CH3:1]Participants
5
Conditions
- Temperature
- 0 °C
Procedure
A solution of (S)-5-methoxy-1-phenyl-1-((R)-piperidin-3-yl)pentan-1-ol (455.6 mg, 1.8 mmol) and triethylamine (1.50 mL, 10.7 mmol) in CH2Cl2 (100 mL) was cooled to 0° C. A solution of triphosgene (278.6 mg, 1.0 mmol) in CH2Cl2 (10 mL) was added with fast dropwise addition. The solution was stirred for 30 min at 0° C. and then for 2 h at rt. The reaction mixture was cooled to 0° C., washed with ice-cold satd aq NaHCO3 (3×10 mL) and ice-cold brine (3×10 mL), dried (Na2SO4), decanted, and stripped to afford (R)-3-((S)-1-hydroxy-5-methoxy-1-phenylpentyl)piperidine-1-carbonyl chloride (540.8 mg, 99%) as a yellow oil. This material was carried on directly to the next step.
Workup
- waitfor 2 h at rt
- temperatureThe reaction mixture was cooled to 0° C.
- washwashed with ice-cold satd aq NaHCO3 (3×10 mL) and ice-cold brine (3×10 mL)
- dry with materialdried (Na2SO4)
- customdecanted
Sources & evidence
- ORD record
- ord-f82cb878b5b3457ba53da65ce6d359f3
- Source dataset
- uspto-grants-2010_07
- Patent number
- US07754737B2
Reaction notes
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