Tetrahydrofuran → HCID 67188838, compound

HRID 545641Notes

Reaction equation

HRID 545641 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][CH:9]2[CH2:14][CH2:13][N:12]([C:15]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16])[CH2:11][CH2:10]2)=[C:4]([C:22]#[N:23])[CH:3]=1.C1COCC1>>[NH2:23][CH2:22][C:4]1[CH:3]=[C:2]([Br:1])[CH:7]=[CH:6][C:5]=1[NH:8][CH:9]1[CH2:10][CH2:11][N:12]([C:15]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16])[CH2:13][CH2:14]1

Participants

3

Reactant 2

HCID 8028TetrahydrofuranHCID 67188470HCID 67188470, compound

Product 1

HCID 67188838HCID 67188838, compound

Procedure

A solution of tert-butyl 4-(4-bromo-2-cyanophenylamino)piperidine-1-carboxylate (1.00 g, 3 mmol) in THF (10 ml, 123 mmol) under argon was added borane-tetrahydrofuran complex (8 ml, 8 mmol) and stirred at RT for 20 h. The reaction was cooled to 0° C. and quenched with MeOH. The mixture was further diluted with EtOAc and washed with saturated aqueous NaHCO3 and brine, then dried (MgSO4). Evaporation gave a relatively pure crop of the desired product, tert-butyl 4-(2-(aminomethyl)-4-bromophenylamino)piperidine-1-carboxylate, which was used directly in the next step without further purification. MS m/e 385.2 (M+H)+.

Workup

  1. temperatureThe reaction was cooled to 0° C.
  2. customquenched with MeOH
  3. additionThe mixture was further diluted with EtOAc
  4. washwashed with saturated aqueous NaHCO3 and brine
  5. dry with materialdried (MgSO4)
  6. customEvaporation

Sources & evidence

ORD record
ord-b0f2decdd279429a84e6ad0661a71423
Source dataset
uspto-grants-2011_05
Patent number
US07935709B2

Reaction notes

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