Water → (6-[(1-Benzyl-3-pyrrolidinyl)amino]-3-pyridyl)methanol

HRID 226294Notes

Reaction equation

[H-].[Al+3].[Li+].[H-].[H-].[H-].[CH2:7]([N:14]1[CH2:18][CH2:17][CH:16]([NH:19][C:20]2[CH:29]=[CH:28][C:23]([C:24](OC)=[O:25])=[CH:22][N:21]=2)[CH2:15]1)[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1.O.[OH-].[Na+]>C1COCC1>[CH2:7]([N:14]1[CH2:18][CH2:17][CH:16]([NH:19][C:20]2[N:21]=[CH:22][C:23]([CH2:24][OH:25])=[CH:28][CH:29]=2)[CH2:15]1)[C:8]1[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=1

Participants

Conditions

Temperature: 7.5 °C

Procedure

Lithium aluminium hydride (256 mg) was added to absolution of methyl 6-[(1-benzyl-3-pyrrolidinyl)amino]nicotinate (1.4 g) in THF (50 ml) with stirring at 5-10° C. under atmospheric pressure of nitrogen, and the reaction mixture was stirred at 5-20° C. for 4 hours. The reaction mixture was cooled at 5° C. and water (0.26 ml), 15% NaOH solution (0.26 ml) and water (0.72 ml) was added, the resultant mixture was stirred at ambient temperature for 20 minutes. The reaction mixture was filtrated and the filtrate was dried over MgSO4. The solvent was evaporated in vacuo and the residue was chromatographed on silicagel eluting with AcOEt-MeOH (85:15). The eluted fractions containing the desired product were collected and evaporated in vacuo to give {6-[(1-benzyl-3-pyrrolidinyl)amino]-3-pyridyl}methanol (0.96 g)

Workup

stirringthe reaction mixture was stirred at 5-20° C. for 4 hours
temperatureThe reaction mixture was cooled at 5° C.
filtrationThe reaction mixture was filtrated
dry with materialthe filtrate was dried over MgSO4
customThe solvent was evaporated in vacuo
customthe residue was chromatographed on silicagel
washeluting with AcOEt-MeOH (85:15)
additionThe eluted fractions containing the desired product
customwere collected
customevaporated in vacuo

Sources & evidence

ORD record: ord-a1e7270e151049d4a9f335f0d0f3ba8a
Source dataset: uspto-grants-2009_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07557127B2

Reaction notes

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