Hydrochloric Acid → HCID 86591142, compound

HRID 1391508Notes

Reaction equation

HRID 1391508 reaction equation
[C:1]1([C:37]2[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=2)[CH:6]=[CH:5][C:4]([C:7]([O:9][C@@H:10]2[C@@H:15]([C:16]3[CH:21]=[CH:20][CH:19]=[C:18]([O:22][Si](C(C)(C)C)(C)C)[CH:17]=3)[CH2:14][CH2:13][N:12](C(OC(C)(C)C)=O)[CH2:11]2)=[O:8])=[CH:3][CH:2]=1.C(OCC)C.[ClH:48]>>[ClH:48].[C:1]1([C:37]2[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=2)[CH:6]=[CH:5][C:4]([C:7]([O:9][C@@H:10]2[C@@H:15]([C:16]3[CH:21]=[CH:20][CH:19]=[C:18]([OH:22])[CH:17]=3)[CH2:14][CH2:13][NH:12][CH2:11]2)=[O:8])=[CH:3][CH:2]=1

Participants

4

Reactant 3

HCID 313Hydrochloric AcidHCID 3283Diethyl EtherHCID 86591141HCID 86591141, compound

Product 1

HCID 86591142HCID 86591142, compound

Procedure

The (+/−)-tert-butyl (3R,4R)-3-[(1,1′-biphenyl-4-ylcarbonyl)oxy]-4-(3-{[tert-butyl(dimethyl)silyl]oxy}phenyl)piperidine-1-carboxylate (91 mg, 0.16 mmol) was dissolved in 4 N Hydrogen chloride in dioxanes (3.0 mL). The solution was stirred for 4 H at room temperature and diethylether (10 mL) was added. The solution was kept at room temperature for 16 H and solids formed. The (+/−)-(3R,4R)-4-(3-hydroxyphenyl)piperidin-3-yl 1,1′-biphenyl-4-carboxylate hydrochloride (56 mg, 0.13 mmol) was obtained as a white solid. HRMS m/z 374.1753 (calcd for M+H 374.1751.)

Workup

  1. customwas kept at room temperature for 16 H and solids
  2. customformed

Sources & evidence

ORD record
ord-d8340bc096e24c07a9474aa3245b0065
Source dataset
uspto-grants-2008_03
Patent number
US07338965B2

Reaction notes

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