Water → Tert-butyl 4-(1-benzhydrylazetidin-3-yl)-3-(hydroxymethyl)piperazine-1-carboxylate

HRID 588889Notes

Reaction equation

[H-].[H-].[H-].[H-].[Li+].[Al+3].[CH:7]([N:20]1[CH2:23][CH:22]([N:24]2[CH2:29][CH2:28][N:27]([C:30]([O:32][C:33]([CH3:36])([CH3:35])[CH3:34])=[O:31])[CH2:26][CH:25]2[C:37](OC)=[O:38])[CH2:21]1)([C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1.O.[OH-].[Na+]>C1COCC1>[CH:7]([N:20]1[CH2:23][CH:22]([N:24]2[CH2:29][CH2:28][N:27]([C:30]([O:32][C:33]([CH3:34])([CH3:35])[CH3:36])=[O:31])[CH2:26][CH:25]2[CH2:37][OH:38])[CH2:21]1)([C:14]1[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=1)[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1

Participants

Conditions

Temperature: -20 °C

Procedure

To a mixture of LiAlH4 (500 mg, 13.5 mmol) in THF (40 mL) at −40° C. under argon, a solution of 1-tert-butyl 3-methyl 4-(1-benzhydrylazetidin-3-yl)piperazine-1,3-dicarboxylate (1.8 g, 3.87 mmol) in THF (10 mL) was added dropwise. The reaction mixture was stirred at −5° C. to 5° C. for 1 h and cooled to −20° C. Then water (2 mL) and NaOH (15%) aqueous were added. The resulting mixture was stirred for 15 min. The solid was filtered, and the cake rinsed with ethyl acetate. The combined filtrate was dried over Na2SO4 and concentrated in vacuo to afford the product (1.6 g, 94% yield).

Workup

stirringThe resulting mixture was stirred for 15 min
filtrationThe solid was filtered
washthe cake rinsed with ethyl acetate
dry with materialThe combined filtrate was dried over Na2SO4
concentrationconcentrated in vacuo

Sources & evidence

ORD record: ord-7fb7f85de40d45fabbaa66fc065015e3
Source dataset: uspto-grants-2016_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09227978B2

Reaction notes

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