Triethylamine → Tert-butyl 4-(((4-nitrophenoxy)carbonyl)oxy)piperidine-1-carboxylate

HRID 449377Notes

Reaction equation

HRID 449377 reaction equation
[OH:1][CH:2]1[CH2:7][CH2:6][N:5]([C:8]([O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[O:9])[CH2:4][CH2:3]1.C(N(CC)CC)C.Cl[C:23]([O:25][C:26]1[CH:31]=[CH:30][C:29]([N+:32]([O-:34])=[O:33])=[CH:28][CH:27]=1)=[O:24]>C(Cl)Cl>[N+:32]([C:29]1[CH:30]=[CH:31][C:26]([O:25][C:23]([O:1][CH:2]2[CH2:3][CH2:4][N:5]([C:8]([O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[O:9])[CH2:6][CH2:7]2)=[O:24])=[CH:27][CH:28]=1)([O-:34])=[O:33]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 821294-Nitrophenyl chloroformateHCID 643502Tert-butyl 4-hydroxypiperidine-1-carboxylate

Product 1

HCID 23536851Tert-butyl 4-(((4-nitrophenoxy)carbonyl)oxy)piperidine-1-carboxylateYield 58.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a mixture of tert-butyl 4-hydroxypiperidine-1-carboxylate (0.30 g, 0.0015 mol) (Aldrich Cat. #495484) and triethylamine (0.31 mL, 0.0022 mol) in methylene chloride (2 mL) was added p-nitrophenyl chloroformate (0.33 g, 0.0016 mol) (Acros Organics, Cat. #17080). The mixture was stirred at r.t. for 2 h. After removal of the solvent under reduced pressure, the residue was purified by flash chromatography on a silica gel with ethyl acetate in hexanes (0-20%) to afford the desired product (0.32 g, 58%). Analytic LCMS (M+Na)+: m/z=389.0.

Workup

  1. customAfter removal of the solvent under reduced pressure
  2. customthe residue was purified by flash chromatography on a silica gel with ethyl acetate in hexanes (0-20%)

Sources & evidence

ORD record
ord-a5e12276858a4601857820a66af27445
Source dataset
uspto-grants-2013_07
Patent number
US08481732B2

Reaction notes

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