Triethylamine → HCID 178453895, compound

HRID 331399Notes

Reaction equation

HRID 331399 reaction equation
[O:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[C:9](C3CCNCC3)[C:4]=2[CH:3]=[CH:2]1.[C:16]([O:20][C:21](=[O:32])[NH:22][C@H:23]1[CH2:28][CH2:27][C@H:26]([CH2:29][CH:30]=O)[CH2:25][CH2:24]1)([CH3:19])([CH3:18])[CH3:17].C([N:35]([CH2:38][CH3:39])[CH2:36][CH3:37])C.[C:40](=O)(O)[O-].[Na+]>ClCCl>[C:16]([O:20][C:21](=[O:32])[NH:22][C@H:23]1[CH2:28][CH2:27][C@H:26]([CH2:29][CH2:30][N:35]2[CH2:36][CH2:37][CH2:40][CH2:39][CH:38]2[C:7]2[CH:6]=[CH:5][O:1][C:2]3[C:8]=2[CH:9]=[CH:4][CH:3]=3)[CH2:25][CH2:24]1)([CH3:19])([CH3:18])[CH3:17]

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 516892Sodium BicarbonateHCID 67972433HCID 67972433, compoundHCID 178453924HCID 178453924, compound

Product 1

HCID 178453895HCID 178453895, compoundYield 99%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of 4-(4-benzofuranyl)-piperidine (0.3 g, 1.49 mmol) in dichloromethane (8 ml) was added at room temperature commercially available trans-tert-butyl-4-(2-oxoethyl)-cyclohexylcarbamate (1.71 mg, 6.02 mmol) and triethylamine (0.3 g, 0.42 ml, 2.98 mmol) and the solution was allowed to stir for 30 min. Sodium triacetoxyboron hydride (0.57 g, 2.68 mmol) was added step wise and the mixture was allowed to stir for 16 h at room temperature. The solution was poured into saturated sodium bicarbonate solution (20 ml) and extracted with dichloromethane (2×40 ml). The combined organic layers were washed with saturated sodium bicarbonate solution (20 ml), dried (MgSO4) and evaporated. The crude material (0.77 g) was purified by flash chromatography on silica gel (dichloromethane/MeOH 5-10%) to yield trans-{4-[2-(4-benzofuran-4-yl-piperidin-1-yl)-ethyl]-cyclohexyl}-carbamic acid tert-butyl ester as a white solid (0.63 g, 99%), MS (ISP) m/z=427.4 [(M+H)+], mp 133° C.

Workup

  1. stirringto stir for 16 h at room temperature
  2. extractionextracted with dichloromethane (2×40 ml)
  3. washThe combined organic layers were washed with saturated sodium bicarbonate solution (20 ml)
  4. dry with materialdried (MgSO4)
  5. customevaporated
  6. customThe crude material (0.77 g) was purified by flash chromatography on silica gel (dichloromethane/MeOH 5-10%)

Sources & evidence

ORD record
ord-31bb30d1cac142f0aec5f453e9e99bef
Source dataset
uspto-grants-2014_11
Patent number
US08877778B2

Reaction notes

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