Ammonium Chloride → HCID 58456731, compound

HRID 2036140Notes

Reaction equation

HRID 2036140 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([C:10]2(O)[CH2:15][CH2:14][N:13]([C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])[CH2:12][CH2:11]2)[CH:5]=[C:6]([F:9])[C:7]=1[OH:8].CCN(S(F)(F)[F:30])CC.[NH4+].[Cl-]>ClCCl>[F:1][C:2]1[CH:3]=[C:4]([C:10]2([F:30])[CH2:15][CH2:14][N:13]([C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])[CH2:12][CH2:11]2)[CH:5]=[C:6]([F:9])[C:7]=1[OH:8]

Participants

5

Reactant 3

HCID 25517Ammonium ChlorideHCID 123472(Diethylamino)sulfur trifluorideHCID 58456720HCID 58456720, compound

Product 1

HCID 58456731HCID 58456731, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

In a plastic container, a solution of tert-butyl 4-(3,5-difluoro-4-hydroxyphenyl)-4-hydroxypiperidine-1-carboxylate D1f (0.4 g, 1.2 mmol) in dichloromethane (10 mL) is treated with DAST (0.31 mL, 2.4 mmol) at room temperature. The mixture is stirred for 30 min and treated with sat. aqueous NH4Cl (3 mL). The mixture is extracted with dichloromethane, washed with sat. aqueous NaHCO3, dried over Na2SO4 and concentrated in vacuo to yield tert-butyl 4-(3,5-difluoro-4-hydroxyphenyl)-4-fluoropiperidine-1-carboxylate D1g as an oil. 1H-NMR (400 MHz, CDCl3) δ=7.01 (d, J=7.2 Hz, 2H), 4.03 (br. s, 2H), 3.19 (br. s, 2H), 1.88 td, J=13.3, 4.8 Hz, 2H), 1.66 (dq, J=14.1, 2.2 Hz, 2H), 1.47 (s, 9H); 19F-NMR (376 MHz, CDCl3) δ=−134.1 (2F), −161.9 (1F). LCMS calcd. for C16H21F3NO3+ ([M+H]+): 332.1, found: 331.8. The product is used without purification.

Workup

  1. extractionThe mixture is extracted with dichloromethane
  2. washwashed with sat. aqueous NaHCO3
  3. dry with materialdried over Na2SO4
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-1aff15627f984a5596d82e4ce9a0f6ed
Source dataset
uspto-grants-2013_11
Patent number
US08575168B2

Reaction notes

Loading…