Diisopropylethylamine → (S)-tert-Butyl 2-(4-(4-(4-fluorophenyl)-1H-1,2,3-triazol-1-yl)phenyl)morpholine-4-carboxylate

HRID 710262Notes

Reaction equation

HRID 710262 reaction equation
[N:1]([C:4]1[CH:9]=[CH:8][C:7]([C@@H:10]2[O:15][CH2:14][CH2:13][N:12]([C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])[CH2:11]2)=[CH:6][CH:5]=1)=[N+:2]=[N-:3].C(N(C(C)C)CC)(C)C.[C:32]([C:34]1[CH:39]=[CH:38][C:37]([F:40])=[CH:36][CH:35]=1)#[CH:33]>[Cu]I>[F:40][C:37]1[CH:38]=[CH:39][C:34]([C:32]2[N:3]=[N:2][N:1]([C:4]3[CH:9]=[CH:8][C:7]([C@@H:10]4[O:15][CH2:14][CH2:13][N:12]([C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])[CH2:11]4)=[CH:6][CH:5]=3)[CH:33]=2)=[CH:35][CH:36]=1

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 5226271-Ethynyl-4-fluorobenzeneHCID 89689527(S)-tert-butyl 2-(4-azidophenyl)morpholine-4-carboxylate

Product 1

HCID 131733930(S)-tert-Butyl 2-(4-(4-(4-fluorophenyl)-1H-1,2,3-triazol-1-yl)phenyl)morpholine-4-carboxylateYield 16%

Reagents, catalysts & solvents 1

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)Catalyst

Procedure

(S)-tert-Butyl 2-(4-azidophenyl)morpholine-4-carboxylate (76 mg, 0.25 mol) was dissolved in diisopropylethylamine (800 mg, 6.24 mmol). 1-Ethinyl-4-fluorobenzene (30 mg, 0.25 mmol) was added, followed by copper(I)-iodide (48 mg, 0.25 mmol). The mixture was stirred for 2 h at room temperature. The green mixture was concentrated on the rotavap, silica gel (0.5 g) was added and after short grinding the mixture was put on a silica gel column for purification. Flash chromatography (5 g silica gel, 10 to 30% ethyl acetate in heptane) yielded a white solid (17 mg, 16%), MS (ISP): 425.2 ([M+H]+).

Workup

  1. concentrationThe green mixture was concentrated on the rotavap, silica gel (0.5 g)
  2. additionwas added
  3. customafter short grinding the mixture
  4. customwas put on a silica gel column for purification

Sources & evidence

ORD record
ord-30c3f26a668f440fb72d78ee1f1bcbf4
Source dataset
uspto-grants-2015_11
Patent number
US09181230B2

Reaction notes

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