Water → (S)-(1-methylpiperazin-2-yl)methanol

HRID 639994Notes

Reaction equation

[H-].[Al+3].[Li+].[H-].[H-].[H-].C(O[C:12]([N:14]1[CH2:19][CH2:18][NH:17][CH2:16][C@H:15]1[C:20](O)=[O:21])=O)(C)(C)C.O.[OH-].[Na+]>O1CCCC1>[CH3:12][N:14]1[CH2:19][CH2:18][NH:17][CH2:16][C@H:15]1[CH2:20][OH:21]

Participants

Conditions

Temperature: 15 °C

Procedure

A solution of lithium aluminium hydride in tetrahydrofuran (1M, 22.0 ml, 22.0 mmol) was added dropwise to a solution of (2S)-1-(tert-butoxycarbonyl)piperazine-2-carboxylic acid (see U.S. Pat. No. 5,348,955, 1.007 g, 4.38 mmol) in tetrahydrofuran (20 ml) cooled to −15° C. The mixture was allowed to warm to 15° C. over 1.5 hours and then heated at reflux for 3 hours. The mixture was cooled in an ice bath and then water (0.4 ml) was added dropwise followed by a dilute solution of sodium hydroxide (1M, 0.4 ml) and a further portion of water (1.2 ml). The mixture was stirred at room temperature for 0.5 hours and then allowed to stand overnight. The resultant precipitate was filtered and the residue was washed with diethyl ether. The filtrate was evaporated and the residue purified by silica gel chromatography eluting with a 10% mixture of methanol (containing 10% 7M ammonia in methanol) in dichloromethane to give [(2S)-1-methylpiperazin-2-yl]methanol (0.3802 g, 67% yield):

Workup

temperatureheated
temperatureat reflux for 3 hours
temperatureThe mixture was cooled in an ice bath
waitto stand overnight
filtrationThe resultant precipitate was filtered
washthe residue was washed with diethyl ether
customThe filtrate was evaporated
customthe residue purified by silica gel chromatography
washeluting with a 10% mixture of methanol (containing 10% 7M ammonia in methanol) in dichloromethane

Sources & evidence

ORD record: ord-7d5999fde7734596a16e3f7bdd70f1b2
Source dataset: uspto-grants-2010_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07691867B2

Reaction notes

Loading…