Dichloromethane → 1,1,1-trifluoro-2-(4-((2R)-2-(hydroxymethyl)-4-(2-thiophenylsulfonyl)-1-piperazinyl)phenyl)-2-propanol

HRID 1972337Notes

Reaction equation

C([O:8][CH2:9][C@H:10]1[CH2:15][N:14]([S:16]([C:19]2[S:20][CH:21]=[CH:22][CH:23]=2)(=[O:18])=[O:17])[CH2:13][CH2:12][N:11]1[C:24]1[CH:29]=[CH:28][C:27]([C:30]([OH:36])([CH3:35])[C:31]([F:34])([F:33])[F:32])=[CH:26][CH:25]=1)C1C=CC=CC=1.C(Cl)Cl.B(Cl)(Cl)Cl>CO>[F:34][C:31]([F:32])([F:33])[C:30]([C:27]1[CH:28]=[CH:29][C:24]([N:11]2[CH2:12][CH2:13][N:14]([S:16]([C:19]3[S:20][CH:21]=[CH:22][CH:23]=3)(=[O:17])=[O:18])[CH2:15][C@@H:10]2[CH2:9][OH:8])=[CH:25][CH:26]=1)([OH:36])[CH3:35]

Participants

Conditions

Temperature: 0 °C

Procedure

A 2-L round-bottomed flask was charged with 2-(4-((2R)-2-((benzyloxy)methyl)-4-(2-thiophenylsulfonyl)-1-piperazinyl)phenyl)-1,1,1-trifluoro-2-propanol (54.4 g, 101 mmol) and 200 mL of CH2Cl2. After cooling to 0° C., BCl3 (1M in CH2Cl2, 302 mL, 302 mmol, Sigma-Aldrich, St. Louis, Mo.) was added over 10 min. After 30 min at 0° C., the mixture was carefully diluted with MeOH and then concentrated and purified via column chromatography on silica gel (0 to 3% MeOH in CH2Cl2) to give 1,1,1-trifluoro-2-(4-((2R)-2-(hydroxymethyl)-4-(2-thiophenylsulfonyl)-1-piperazinyl)phenyl)-2-propanol (42.7 g) as a tan foam.

Workup

concentrationconcentrated
custompurified via column chromatography on silica gel (0 to 3% MeOH in CH2Cl2)

Sources & evidence

ORD record: ord-342a2424e5b64e53811ea3b9ebb92625
Source dataset: uspto-grants-2013_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08431563B2

Reaction notes

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