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Triethylamine → HCID 178453909, compound

HRID 1260704
Notes
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Reaction equation

HRID 1260704 reaction equation
[N:1]1([C:7]2[N:8]=[CH:9][CH:10]=[C:11]3[CH2:15][CH2:14][O:13][C:12]=23)[CH2:6][CH2:5][NH:4][CH2:3][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(N(CC)CC)C>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:4]2[CH2:3][CH2:2][N:1]([C:7]3[N:8]=[CH:9][CH:10]=[C:11]4[CH2:15][CH2:14][O:13][C:12]=34)[CH2:6][CH2:5]2)[CH2:27][CH2:28]1)([CH3:19])([CH3:18])[CH3:17]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 666534657-(Piperazin-1-yl)-2,3-dihydro-furo[2,3-c]pyridineHCID 178453924HCID 178453924, compound

Product 1

HCID 178453909HCID 178453909, compoundYield 65%

Reagents, catalysts & solvents 2

HCID 887MethanolSolvent
HCID 6344
Dichloromethane
Solvent

Procedure

To a solution of 7-(piperazin-1-yl)-2,3-dihydro-furo[2,3-c]pyridine (0.96 g, 4.68 mmol) in dichloromethane (30 ml) and MeOH (0.8 ml) was added at room temperature commercially available trans-tert-butyl-4-(2-oxoethyl)-cyclohexylcarbamate (1.71 mg, 6.02 mmol) and triethylamine (1.02 g, 1.4 ml, 10 mmol) and the solution was allowed to stir for 30 min. Sodium triacetoxyboron hydride (1.91 g, 9.03 mmol) was added step wise and the mixture was allowed to stir for 4 h at room temperature. The solution was added to ice/2N sodium carbonate solution (50 ml), extracted with dichloromethane (2×30 ml). The combined organic layers were dried (MgSO4) and evaporated. The crude material (2.53 g) was purified by flash chromatography on silica gel (20% to 100% dichloromethane/dichloromethane-MeOH 9:1) to yield trans-(4-{2-[4-(2,3-dihydro-furo[2,3-c]pyridin-7-yl)-piperazin-1-yl]-ethyl}-cyclohexyl)-carbamic acid tert-butyl ester as off-white solid (1.3 g, 65%), MS (ISP) m/z=431.5 [(M+H)+], mp 141° C.

Workup

  1. stirringto stir for 4 h at room temperature
  2. extractionextracted with dichloromethane (2×30 ml)
  3. dry with materialThe combined organic layers were dried (MgSO4)
  4. customevaporated
  5. customThe crude material (2.53 g) was purified by flash chromatography on silica gel (20% to 100% dichloromethane/dichloromethane-MeOH 9:1)

Sources & evidence

ORD record
ord-8ac37e19590746bc98cf7741d7bfa601
Source dataset
uspto-grants-2013_06
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08470828B2

Reaction notes

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