Toluene → 4-[4-(tert-Butoxycarbonyl)piperazin-1-yl]benzyl alcohol

HRID 54222Notes

Reaction equation

HRID 54222 reaction equation
[H-].C([Al+]CC(C)C)C(C)C.C1(C)C=CC=CC=1.[C:18]([O:22][C:23]([N:25]1[CH2:30][CH2:29][N:28]([C:31]2[CH:36]=[CH:35][C:34]([C:37](OC)=[O:38])=[CH:33][CH:32]=2)[CH2:27][CH2:26]1)=[O:24])([CH3:21])([CH3:20])[CH3:19]>C1COCC1>[C:18]([O:22][C:23]([N:25]1[CH2:26][CH2:27][N:28]([C:31]2[CH:32]=[CH:33][C:34]([CH2:37][OH:38])=[CH:35][CH:36]=2)[CH2:29][CH2:30]1)=[O:24])([CH3:21])([CH3:19])[CH3:20]

Participants

5

Reactant 3

HCID 1140TolueneHCID 27955131-Boc-4-(4-methoxycarbonylphenyl)piperazineHCID 21225700Diisobutylaluminumhydride

Product 1

HCID 27955104-[4-(tert-Butoxycarbonyl)piperazin-1-yl]benzyl alcoholYield 86.9%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

Diisobutylaluminium hydride in toluene (1.5M, 15 ml, 22.5 mmol) was added dropwise to a solution of 1-(tert-butoxycarbonyl)-4-(4-methoxycarbonylphenyl)piperazine (2.90 g, 9.05 mmol) in THF (116 ml) at 0° C. The mixture was stirred at 0° C. for 2 hours then allowed to warm to room temperature. The solution was recooled to -4° C. and the reaction quenched by the addition of methanol (6 ml), water (3 ml) and finally 2M sodium hydroxide (3 ml). The mixture was allowed to warm to room temperature, the precipitated aluminium salts collected under suction and washed with dichloromethane. The filtrate was concentrated in vacuo and the residue purified by flash chromatography, eluting with dichloromethane/ethyl acetate, to give the title compound (2.30 g, 74%); δH (CDCl8) 1.48 (9H, s, C(CH3)8), 1.60 (1H, v br, CH2OH), 3.13 (4H, m, 2×piperazinyl CH2), 3.58 (4H, m, 2×piperazinyl CH2), 4.61 (2H, s, CH2OH), 6.92 (2H, m, ArH), and 7.29 (2H, m, ArH).

Workup

  1. temperatureto warm to room temperature
  2. customwas recooled to -4° C.
  3. customthe reaction quenched by the addition of methanol (6 ml), water (3 ml) and finally 2M sodium hydroxide (3 ml)
  4. temperatureto warm to room temperature
  5. customthe precipitated aluminium salts collected under suction
  6. washwashed with dichloromethane
  7. concentrationThe filtrate was concentrated in vacuo
  8. customthe residue purified by flash chromatography
  9. washeluting with dichloromethane/ethyl acetate

Sources & evidence

ORD record
ord-1fdfa88aac7842a4b5052577e632a34f
Source dataset
uspto-grants-1997_04
Patent number
US05622950

Reaction notes

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