Sodium Bicarbonate → HCID 178453890, compound

HRID 1909358Notes

Reaction equation

HRID 1909358 reaction equation
[O:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[C:9]([CH:10]3[CH2:15][CH2:14][NH:13][CH2:12][CH2:11]3)[C:4]=2[O:3][CH2:2]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(=O)(O)[O-].[Na+]>ClCCl.CO>[C:16]([O:20][C:21](=[O:32])[NH:22][C@H:23]1[CH2:24][CH2:25][C@H:26]([CH2:29][CH2:30][N:13]2[CH2:14][CH2:15][CH:10]([C:9]3[C:4]4[O:3][CH2:2][O:1][C:5]=4[CH:6]=[CH:7][CH:8]=3)[CH2:11][CH2:12]2)[CH2:27][CH2:28]1)([CH3:19])([CH3:18])[CH3:17]

Participants

6

Reactant 3

HCID 516892Sodium BicarbonateHCID 706572904-Benzo[1,3]dioxol-4-yl-piperidineHCID 178453924HCID 178453924, compound

Product 1

HCID 178453890HCID 178453890, compoundYield 100.3%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of 4-Benzo[1,3]dioxol-4-yl-piperidine (0.680 g, 3.31 mmol,) in dichloromethane (35 ml) and methanol (1 ml) was added at room temperature commercially available trans-tert-butyl-4-(2-oxoethyl)-cyclohexylcarbamate (1.04 g, 4.31 mmol) and the solution was allowed to stir for 120 min. Sodium triacetoxyboron hydride (1.26 g, 5.96 mmol) was added portion wise and the mixture was allowed to stir for 16 h at room temperature. The solution was poured into saturated sodium bicarbonate solution (15 ml) and extracted with dichloromethane (2×20 ml). The combined organic layers were dried (MgSO4) and evaporated. The crude material was purified by flash chromatography on silica gel The crude material was purified by flash chromatography (methanol in dichloromethane 0-10%) to yield trans-{4-[2-(4-Benzo[1,3]dioxol-4-yl-piperidin-1-yl)-ethyl]-cyclohexyl}-carbamic acid tert-butyl ester as a white solid (1.43 g, 74%), MS (ISP) m/z=431.5 [(M+H)+].

Workup

  1. stirringto stir for 16 h at room temperature
  2. extractionextracted with dichloromethane (2×20 ml)
  3. dry with materialThe combined organic layers were dried (MgSO4)
  4. customevaporated
  5. customThe crude material was purified by flash chromatography on silica gel The crude material
  6. customwas purified by flash chromatography (methanol in dichloromethane 0-10%)

Sources & evidence

ORD record
ord-8a3339f7aa444be095b68d24d54f52cc
Source dataset
uspto-grants-2013_12
Patent number
US08598357B2

Reaction notes

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