HCID 59383032, compound → HCID 59382818, compound

HRID 2355394Notes

Reaction equation

HRID 2355394 reaction equation
[C:1]([NH:4][CH2:5][CH2:6][CH2:7][C@:8]([C@@H:17]1[CH2:22][CH2:21][CH2:20][N:19](C(OC(C)(C)C)=O)[CH2:18]1)([C:10]1[CH:15]=[CH:14][CH:13]=[C:12]([Cl:16])[CH:11]=1)[OH:9])(=[O:3])[CH3:2]>CC#N.Cl>[Cl:16][C:12]1[CH:11]=[C:10]([C@@:8]([OH:9])([C@@H:17]2[CH2:22][CH2:21][CH2:20][NH:19][CH2:18]2)[CH2:7][CH2:6][CH2:5][NH:4][C:1](=[O:3])[CH3:2])[CH:15]=[CH:14][CH:13]=1

Participants

4

Reactant 1

HCID 59383032HCID 59383032, compound

Product 1

HCID 59382818HCID 59382818, compound

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 6342AcetonitrileSolvent

Procedure

A mixture of (R)-tert-butyl 3-((S)-4-acetamido-1-(3-chlorophenyl)-1-hydroxybutyl)-piperidine-1-carboxylate (0.1773 g, 0.4172 mmol) in CH3CN (50 mL) and 2 N aq HCl (45 mL) was vigorously stirred at rt for 24 h. The solvents were removed in vacuo to give the HCl salt of N—((S)-4-(3-chlorophenyl)-4-hydroxy-4-((R)-piperidin-3-yl)butyl)acetamide, which was used in the next step without further purification. LC-MS (3 min) tR=0.91 min, m/z 325, 327 (MH+).

Workup

  1. customThe solvents were removed in vacuo

Sources & evidence

ORD record
ord-5ae330f9b6284345b91d62ceba74e50d
Source dataset
uspto-grants-2010_07
Patent number
US07754737B2

Reaction notes

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