Water → 1-Benzyl-4-hydroxymethyl-4-(1,2,4-triazol-1-yl) piperidine

HRID 1602328Notes

Reaction equation

[CH2:1]([N:8]1[CH2:13][CH2:12][C:11]([C:19](OCC)=[O:20])([N:14]2[CH:18]=[N:17][CH:16]=[N:15]2)[CH2:10][CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[H-].[Al+3].[Li+].[H-].[H-].[H-].O.[OH-].[Na+]>CCOCC.C1COCC1>[CH2:1]([N:8]1[CH2:13][CH2:12][C:11]([CH2:19][OH:20])([N:14]2[CH:18]=[N:17][CH:16]=[N:15]2)[CH2:10][CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

Conditions

Temperature: 15 °C

Procedure

A solution of ethyl 1-benzyl-4-(1,2,4-triazol-1-yl)-piperidin-4-ylcarboxylate (D28, 460 mg, 0.00147 mol) in ether (15 ml) was added dropwise to a stirred suspension of lithium aluminium hydride (67 mg, 0.00175 mol) in ether (25 ml) and dry THF (8 ml) at 0° C. under nitrogen. The reaction mixture was allowed to warm to 15° C. over 20 minutes, then treated with water (0.06 ml), followed by 10% sodium hydroxide solution (0.18 ml) and then water (0.06 ml). The grey precipitate was removed by filtration through a pad of Kieselguhr and the filtrate dried (Na2SO4) and concentrated in vacuo to leave a yellow oil. This was purified by passage through a short silica gel column eluting with 10% methanol/ethyl acetate to give the title compound (D29) (320 mg, 80%) as a pale yellow oil.

Workup

customThe grey precipitate was removed by filtration through a pad of Kieselguhr
dry with materialthe filtrate dried (Na2SO4)
concentrationconcentrated in vacuo
customto leave a yellow oil
customThis was purified by passage through a short silica gel column
washeluting with 10% methanol/ethyl acetate

Sources & evidence

ORD record: ord-dc84a70702b2479d87d29502aeda4bf2
Source dataset: uspto-grants-1999_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05981545

Reaction notes

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