Methanol → HCID 24785715, compound

HRID 391473Notes

Reaction equation

HRID 391473 reaction equation
[C:1]([C:3]1[CH:8]=[CH:7][C:6]([C:9]2[CH:14]=[CH:13][C:12]([O:15][CH3:16])=[C:11]([CH2:17][O:18][CH2:19][C:20]3([C:33]4[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=4)[CH2:25][CH2:24][N:23](C(OC(C)(C)C)=O)[CH2:22][CH2:21]3)[CH:10]=2)=[CH:5][CH:4]=1)#[N:2].CO>ClCCl.FC(F)(F)C(O)=O>[CH3:16][O:15][C:12]1[CH:13]=[CH:14][C:9]([C:6]2[CH:5]=[CH:4][C:3]([C:1]#[N:2])=[CH:8][CH:7]=2)=[CH:10][C:11]=1[CH2:17][O:18][CH2:19][C:20]1([C:33]2[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=2)[CH2:25][CH2:24][NH:23][CH2:22][CH2:21]1

Participants

5

Reactant 2

HCID 887Methanol2×HCID 58993539HCID 58993539, compound

Product 1

HCID 24785715HCID 24785715, compound

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 6422Trifluoroacetic acidSolvent

Procedure

tert-Butyl 4-(((4′-cyano-4-methoxybiphenyl-3-yl)methoxy)methyl)-4-phenylpiperidine-1-carboxylate (47 mg, 0.092 mmol) was dissolved in dichloromethane (2 mL) and trifluoroacetic acid (1 mL). The reaction was stirred for 45 min and concentrated. The residue was dissolved in methanol and loaded onto an strong cation exchange cartridge. The cartridge was flushed with plenty of methanol which was discarded. The product was then eluted using 2 M ammonia in methanol. The solvent was evaporated to give 34 mg (90%) as a colorless oil. Retention time: 2.20 min. (Phenomenex C18 3.0×50 mm, 10% MeOH/90% H2O/0.1% TFA→90% MeOH/10% H2O/0.1% TFA, Gradient time=3 min., Flow rate=4 mL/min.) Mass spec.: 413.39 (MH)+. Accurate mass spec.: m/z 413.2245 [MH]+, Δ=3.9 ppm.

Workup

  1. concentrationconcentrated
  2. dissolutionThe residue was dissolved in methanol
  3. customThe cartridge was flushed with plenty of methanol which
  4. washThe product was then eluted
  5. customThe solvent was evaporated
  6. customto give 34 mg (90%) as a colorless oil

Sources & evidence

ORD record
ord-e8f0fd20127a4862a58334b6af6ba829
Source dataset
uspto-grants-2013_02
Patent number
US08383821B2

Reaction notes

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