Sodium Bicarbonate → 1-(Benzyl-methyl-amino)-heptan-3-one

HRID 2220345Notes

Reaction equation

[CH2:1]([Li])[CH2:2][CH2:3][CH3:4].[CH2:6]([N:13]([CH3:22])[CH2:14][CH2:15][C:16](N(OC)C)=[O:17])[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1.C(=O)(O)[O-].[Na+]>O1CCCC1>[CH2:6]([N:13]([CH3:22])[CH2:14][CH2:15][C:16](=[O:17])[CH2:1][CH2:2][CH2:3][CH3:4])[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1

Participants

Conditions

Temperature: -40 °C

Procedure

Add butyllithium (12.3 ml (1.6 M solution in hexane), 19.6 mmol) to a stirred solution of 3-(benzyl-methyl-amino)-N-methoxy-N-methyl-propionamide and anhydrous tetrahydrofuran (70 ml) at −40° C. under N2. Stir for 1 hr at −40° C. Quench the reaction with saturated ammonium chloride (25 ml), allow the reaction to reach room temperature and add saturated sodium bicarbonate. Extract with ethyl acetate, wash with brine and dry over sodium sulfate. Filter off and concentrate to give the crude product. Purify the compound by flash chromatography, eluting with 2% ethanol/0.2% ammonium hydroxide/chloroform to yield 2.41 g (81%) of 1-(benzyl-methyl-amino)-heptan-3-one: mass spectrum (ion spray) m/z=234 (M+1); 1H NMR (CDCl3) δ 7.31-7.24 (m, 5H), 3.5 (s, 2H), 2.74-2.7 (m, 2H), 2.64-2.60 (m, 2H), 2.41 (t, 2H), 2.19 (s, 3H), 1.59-1.51 (m, 2H), 1.35-1.28 (m, 2H), 0.91 (t, 3H).

Workup

customQuench
customthe reaction with saturated ammonium chloride (25 ml)
customthe reaction
customto reach room temperature
extractionExtract with ethyl acetate
washwash with brine
dry with materialdry over sodium sulfate
filtrationFilter off
concentrationconcentrate
customto give the crude product
customPurify the compound by flash chromatography
washeluting with 2% ethanol/0.2% ammonium hydroxide/chloroform

Sources & evidence

ORD record: ord-5b398ec56e514f16b25250b13ba80e45
Source dataset: uspto-grants-2008_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07417064B2

Reaction notes

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