Formate → HCID 58728712, compound

HRID 1992067Notes

Reaction equation

HRID 1992067 reaction equation
C(O)(C(F)(F)F)=O.[CH3:8][O:9][C:10]1[CH:27]=[CH:26][C:13]([CH2:14][C:15]2[N:19]=[C:18]([CH:20]3[CH2:25][CH2:24][NH:23][CH2:22][CH2:21]3)[O:17][N:16]=2)=[CH:12][CH:11]=1.[C:28]([N:36]1[CH2:41][CH2:40][C:39]([CH2:48][CH:49]=O)([C:42]2[CH:47]=[CH:46][CH:45]=[CH:44][CH:43]=2)[CH2:38][CH2:37]1)(=[O:35])[C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1.[BH-](OC(C)=O)(OC(C)=O)OC(C)=O.[Na+].C([O-])(O)=O.[Na+].C([O-])=O>C(Cl)Cl>[C:28]([N:36]1[CH2:37][CH2:38][C:39]([CH2:48][CH2:49][N:23]2[CH2:24][CH2:25][CH:20]([C:18]3[O:17][N:16]=[C:15]([CH2:14][C:13]4[CH:12]=[CH:11][C:10]([O:9][CH3:8])=[CH:27][CH:26]=4)[N:19]=3)[CH2:21][CH2:22]2)([C:42]2[CH:47]=[CH:46][CH:45]=[CH:44][CH:43]=2)[CH2:40][CH2:41]1)(=[O:35])[C:29]1[CH:30]=[CH:31][CH:32]=[CH:33][CH:34]=1

Participants

8

Reactant 6

HCID 283FormateHCID 6422Trifluoroacetic acidHCID 516892Sodium BicarbonateHCID 5049666Sodium triacetoxyborohydrideHCID 25132605HCID 25132605, compoundHCID 58961103HCID 58961103, compound

Product 1

HCID 58728712HCID 58728712, compoundYield 38%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

The TFA salt of 4-[3-(4-methoxybenzyl)-1,2,4-oxadiazol-5-yl]piperidine (29 mg, 0.076 mmol) was combined with (1-benzoyl-4-phenylpiperidin-4-yl)acetaldehyde (21 mg, 0.069 mmol) in 2 mL DCM and treated with NaBH(OAc)3 (43 mg, 0.203 mmol) at ambient temperature with agitation for 18 h. 1 mL of saturated aqueous NaHCO3 was added and agitated 1 h. The organic phase was separated and concentrated. The crude product was purified by HPLC to give 1-benzoyl-4-(2-{4-[3-(4-methoxybenzyl)-1,2,4-oxadiazol-5-yl]piperidin-1-yl}ethyl)-4-phenylpiperidine (16.1 mg, 0.026 mmol, 38%) as the formate salt. 1H NMR (300 MHz, CD3OD) δ 7.49-7.37 (m, 9H), 7.28 (m, 1H), 7.20 (d, 2H, J=8.8 Hz), 6.86 (d, 2H, J=8.8 Hz), 4.19 (m, 1H), 3.96 (s, 2H), 3.76 (s, 3H), 3.59 (m, 1H), 3.37-3.20 (m, 3H), 3.12-2.95 (m, 3H), 2.45-1.73 (m, 13H). ES-LCMS m/z 565.29 (M+H). HRMS C35H40N4O3 m/z 565.3179 (M+H)Cal. 565.3183 (M+H)Obs..

Workup

  1. customThe organic phase was separated
  2. concentrationconcentrated
  3. customThe crude product was purified by HPLC

Sources & evidence

ORD record
ord-abc6e7b590f846218315f9b73d623d37
Source dataset
uspto-grants-2010_01
Patent number
US07645771B2

Reaction notes

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