Water → HCID 59764769, compound

HRID 406489Notes

Reaction equation

HRID 406489 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[CH:9]1[CH2:14][CH2:13][NH:12][CH2:11][CH2:10]1.[CH:15]1([C@@:18]23[CH:25]=[CH:24][C:23](=[O:26])[N:22]2[C@@H:21]([C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)[CH2:20][O:19]3)[CH2:17][CH2:16]1.O>C(Cl)Cl>[CH:15]1([C@@:18]23[C@H:25]([N:12]4[CH2:13][CH2:14][CH:9]([C:4]5[CH:5]=[CH:6][CH:7]=[CH:8][C:3]=5[O:2][CH3:1])[CH2:10][CH2:11]4)[CH2:24][C:23](=[O:26])[N:22]2[C@@H:21]([C:27]2[CH:28]=[CH:29][CH:30]=[CH:31][CH:32]=2)[CH2:20][O:19]3)[CH2:17][CH2:16]1

Participants

5

Reactant 3

HCID 962WaterHCID 5447384-(2-Methoxyphenyl)piperidineHCID 59764785(3S,7aR)-7a-cyclopropyl-3-phenyl-2,3-dihydropyrrolo[2,1-b]oxazol-5(7aH)-one

Product 1

HCID 59764769HCID 59764769, compoundYield 72.7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a mixture of 4-(2-methoxyphenyl)piperidine (0.951 g, 4.97 mmol) and (3S,7aR)-7a-cyclopropyl-3-phenyl-2,3-dihydropyrrolo[2,1-b]oxazol-5(7aH)-one (preparation #24) (1.0 g, 4.1 mmol) was added water (0.8 mL, 44 mmol). After about 5 minutes, DCM (5 mL) was added. All the solids dissolved. The reaction mixture was stirred at room temperature for about 16 hours. Purification on a Biotage silica gel column eluting with DCM/EtOAc (1:0 to 1:1) afforded (3S,7R,7aR)-7a-cyclopropyl-7-(4-(2-methoxyphenyl)piperidin-1-yl)-3-phenyltetrahydropyrrolo[2,1-b]oxazol-5(6H)-one (1.29 g, 2.98 mmol) as a white solid. RP-HPLC (Table 1, Method a) Rt 2.14 min; m/z: (M+H)+ 433.

Workup

  1. dissolutionAll the solids dissolved
  2. customPurification on a Biotage silica gel column
  3. washeluting with DCM/EtOAc (1:0 to 1:1)

Sources & evidence

ORD record
ord-ad129aedb7d14d178d945b551d998006
Source dataset
uspto-grants-2014_06
Patent number
US08754107B2

Reaction notes

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