Water → (3-{(R*)-1-[(S)-1-(2,3-Dihydrobenzo[1,4]dioxin-2-yl)methyl]piperidin-3-yl}phenyl)methanol

HRID 2365962Notes

Reaction equation

C[O:2][C:3](=O)[C:4]1[CH:9]=[CH:8][CH:7]=[C:6]([C@H:10]2[CH2:15][CH2:14][CH2:13][N:12]([C:16]([C@@H:18]3[O:23][C:22]4[CH:24]=[CH:25][CH:26]=[CH:27][C:21]=4[O:20][CH2:19]3)=O)[CH2:11]2)[CH:5]=1.[H-].[H-].[H-].[H-].[Li+].[Al+3].O.[OH-].[Na+]>C1COCC1>[O:23]1[C:22]2[CH:24]=[CH:25][CH:26]=[CH:27][C:21]=2[O:20][CH2:19][C@@H:18]1[CH2:16][N:12]1[CH2:13][CH2:14][CH2:15][C@H:10]([C:6]2[CH:5]=[C:4]([CH2:3][OH:2])[CH:9]=[CH:8][CH:7]=2)[CH2:11]1

Participants

Conditions

Temperature: 0 °C

Procedure

((R*)-3-[1-((R)-2,3-Dihydrobenzo[1,4]dioxine-2-carbonyl)piperidin-3-yl]benzoic acid methyl ester (54 mg, 0.147 mmol) was dissolved in dry THF (4 ml) and cooled to 0° C. LiAlH4 (26 mg, 0.680 mmol) was added and the mixture was stirred at RT for 2 h. Water (1 ml), 1 M NaOH (1 ml) and again water (1 ml) were added slowly. The mixture was filtered through Celite and evaporated. Flash chromatography, using a gradient of heptane/EtOAc, gave 3.5 mg of the title compound.

Workup

filtrationThe mixture was filtered through Celite
customevaporated

Sources & evidence

ORD record: ord-04d6ab42223e4efb8d9242a8526df6cd
Source dataset: uspto-grants-2014_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08697723B2

Reaction notes

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