Triethylamine → Benzyl 4-{2-[(trans-4-hydroxytetrahydrofuran-3-yl)oxy]ethoxy}piperidine-1-carboxylate

HRID 2359354Notes

Reaction equation

HRID 2359354 reaction equation
[OH:1][CH2:2][CH2:3][O:4][CH:5]1[CH2:10][CH2:9][N:8]([C:11]([O:13][CH2:14][C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)=[O:12])[CH2:7][CH2:6]1.[O:21]1[CH:26]2[CH:22]1[CH2:23][O:24][CH2:25]2.C(N(CC)CC)C>ClCCl>[OH:21][C@@H:22]1[CH2:23][O:24][CH2:25][C@H:26]1[O:1][CH2:2][CH2:3][O:4][CH:5]1[CH2:10][CH2:9][N:8]([C:11]([O:13][CH2:14][C:15]2[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=2)=[O:12])[CH2:7][CH2:6]1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 675113,6-Dioxabicyclo[3.1.0]hexaneHCID 57517495Benzyl 4-(2-hydroxyethoxy)piperidine-1-carboxylate

Product 1

HCID 66990355Benzyl 4-{2-[(trans-4-hydroxytetrahydrofuran-3-yl)oxy]ethoxy}piperidine-1-carboxylateYield 49%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Benzyl 4-(2-hydroxyethoxy)piperidine-1-carboxylate (6.70 g, 24.0 mmol) produced in Reference Example 1 (1b) and 3,4-epoxytetrahydrofuran (1.03 g, 12.0 mmol) were dissolved in dichloromethane (5.0 mL). To the resulting mixture, a boron trifluoride diethyl ether complex (0.34 g, 2.4 mmol) was added at room temperature, followed by stirring for 16 hours. More boron trifluoride diethyl ether complex (0.34 g, 2.4 mmol) was added, followed by further stirring for two hours. Triethylamine (1.82 g, 18.0 mmol) was then added, and the resulting reaction liquid was directly purified by basic silica gel column chromatography (hexane:ethyl acetate, 100:0-0:100, ethyl acetate:methanol, 100:0-95:5, V/V) to give the desired title compound (2.14 g, yield 49%).

Workup

  1. additionTo the resulting mixture, a boron trifluoride diethyl ether complex (0.34 g, 2.4 mmol) was added at room temperature
  2. additionMore boron trifluoride diethyl ether complex (0.34 g, 2.4 mmol) was added
  3. stirringby further stirring for two hours
  4. customthe resulting reaction liquid
  5. customwas directly purified by basic silica gel column chromatography (hexane:ethyl acetate, 100:0-0:100, ethyl acetate:methanol, 100:0-95:5, V/V)

Sources & evidence

ORD record
ord-7b35794fc397423fa349ad96b0dcca1e
Source dataset
uspto-grants-2014_04
Patent number
US08685981B2

Reaction notes

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