Methanol → HCID 7138545, compound

HRID 2112097Notes

Reaction equation

[H-].[Al+3].[Li+].[H-].[H-].[H-].[N:7]1([C@H:12]([CH3:16])[C:13]([NH2:15])=O)[CH2:11][CH2:10][CH2:9][CH2:8]1.CO.ClCCl>C1COCC1>[N:7]1([C@H:12]([CH3:16])[CH2:13][NH2:15])[CH2:11][CH2:10][CH2:9][CH2:8]1

Participants

Conditions

Temperature: 50 °C

Procedure

Under a nitrogen atmosphere 31.65 ml 1 M Lithiumaluminiumhydrid solution (THF) are taken and combined with 1 g (7.032 mmol) (R)-2-pyrrolidin-1-yl-propionamide, dissolved in 2 ml THF, at 0° C. The reaction mixture is stirred for 48 h at 50° C. The reaction mixture is combined with 100 ml of methanol and then with the same amount of dichloromethane while cooling with ice. Approx. 25 g silica gel are added to this mixture and the solvent is eliminated in vacuo. This silica gel applied to a suction filter which has previously been charged with approx. 75 g silica gel. The suction filter is washed batchwise with a total of 500 ml of a mixture of dichloromethane, methanol and aqueous conc. ammonia (90:9:1). The majority of the solvent is eliminated at a vacuum of 200 mbar and a sump temperature of approx. 50° C. The product is distilled at 69-71° C. and 10 mbar.

Workup

additionApprox. 25 g silica gel are added to this mixture
filtrationfilter which
additionhas previously been charged with approx. 75 g silica gel
filtrationThe suction filter
washis washed batchwise with a total of 500 ml of a mixture of dichloromethane, methanol and aqueous conc. ammonia (90:9:1)
customa sump temperature of approx. 50° C
distillationThe product is distilled at 69-71° C.

Sources & evidence

ORD record: ord-d800a7186ffe4d229c58b4039feb284d
Source dataset: uspto-grants-2009_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07521457B2

Reaction notes

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