Water → (2-(2-(Piperidin-1-yl)ethylamino)-3-fluorophenyl)methanol

HRID 1695928Notes

Reaction equation

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

Participants

Conditions

Temperature: 0 °C

Procedure

A solution of methyl 2-(2-(piperidin-1-yl)ethylamino)-3-fluorobenzoate (740 mg, 2.640 mmol) in Et2O (30 mL) at −20° C. was treated with LAH (128 mg, 3.372 mmol). After 1.5 hours additional LAH (20 mg, 0.5269 mmol) was added and the reaction was warmed to 0° C. At 0° C., the reaction was diluted with Et2O (80 mL), then NaF and water were added with vigorous stirring until a white ppt formed and the solution cleared. The solution was decanted and evaporated under vacuum. The crude material was purified on a 12 g Redisep ISCO column with 0-10% MeOH in CH2Cl2 over 40 CV to yield (2-(2-(piperidin-1-yl)ethylamino)-3-fluorophenyl)methanol (453 mg, 179.5 mmol) as an off-white solid. FIA: 253.19 (M+1).

Workup

customformed
customThe solution was decanted
customevaporated under vacuum
customThe crude material was purified on a 12 g Redisep ISCO column with 0-10% MeOH in CH2Cl2 over 40 CV

Sources & evidence

ORD record: ord-6dea3352313440bdbc218d029695ede3
Source dataset: uspto-grants-2012_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08163737B2

Reaction notes

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