Chloroform → (1S)-3-(3-chlorophenyl)-3-cyano-1-(2-[(phenylmethyl)oxy]ethyl}propyl 4-methylbenzenesulfonate
Reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:8]([CH2:11][C@H:12]([OH:23])[CH2:13][CH2:14][O:15][CH2:16][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[C:9]#[N:10])[CH:5]=[CH:6][CH:7]=1.[C:24]1(C)[C:25]([S:30](Cl)(=[O:32])=[O:31])=[CH:26][CH:27]=[CH:28][CH:29]=1.[CH:35](Cl)(Cl)Cl>N1C=CC=CC=1.CN(C1C=CN=CC=1)C>[CH3:35][C:28]1[CH:29]=[CH:24][C:25]([S:30]([O:23][C@H:12]([CH2:13][CH2:14][O:15][CH2:16][C:17]2[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=2)[CH2:11][CH:8]([C:4]2[CH:5]=[CH:6][CH:7]=[C:2]([Cl:1])[CH:3]=2)[C:9]#[N:10])(=[O:31])=[O:32])=[CH:26][CH:27]=1Participants
6
Reactant 3
Product 1
Reagents, catalysts & solvents 2
Procedure
To a solution of (4S)-2-(3-chlorophenyl)-4-hydroxy-6-[(phenylmethyl)oxy]hexanenitrile (6.00 g, 18.2 mmol) in 50% CHCl3 in pyridine at 0° C. was added DMAP (2.22 g) and toluenesulfonyl chloride (10.4 g, 54.5 mmol). After warming to room temperature over several hours, the reaction mixture was stored in the freezer for 2 days. After an aqueous work up with 1N HCl the organic layer was dried over MgSO4 and evaporated to an oil. Chromatography on silica with 25% EtOAc in Hexanes afforded the title compound (5.68 g, 66%) as a yellow oil. 1H NMR (400 MHz, CHLOROFORM-D) δ ppm 1.9 (m, 2H) 2.1 (m, 2H) 2.3 (m, 2H) 2.4 (s, 3H) 3.4 (m, 1H) 3.5 (m, 1H) 4.4 (m, 2H) 7.1 (m, 1H) 7.3 (m, 10H) 7.8 (m, 2H)
Workup
- dry with materialAfter an aqueous work up with 1N HCl the organic layer was dried over MgSO4
- customevaporated to an oil
Sources & evidence
- ORD record
- ord-dd73e190a45840f6a9b124589ed866b1
- Source dataset
- uspto-grants-2009_08
- Patent number
- US07569579B2
Reaction notes
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