Methylamine → HCID 69419650, compound

HRID 1178869Notes

Reaction equation

[CH3:1][NH2:2].[C:3]1(=[O:8])[CH2:7][CH2:6][CH:5]=[CH:4]1.[C:9](OC(O[C:20]([CH3:23])([CH3:22])[CH3:21])=O)([O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:10]>ClCCl>[C:12]([O:8][CH2:3][CH3:7])(=[O:11])[CH3:13].[CH3:3][CH2:4][CH2:23][CH:20]([CH3:21])[CH3:22].[C:12]([O:11][C:9]([CH2:1][NH:2][CH:5]1[CH2:6][CH2:7][C:3](=[O:8])[CH2:4]1)=[O:10])([CH3:15])([CH3:14])[CH3:13]

Participants

Conditions

Temperature: -4 °C

Procedure

Methylamine (2.0M in THF; 40 ml, 80 mmol) was added dropwise over 5 minutes to a solution of 2-cyclopenten-1-one (6.8 ml, 81 mmol) in dichloromethane (70 ml) cooled to −4° C. The resulting mixture was stirred at −4° C. to +1° C. for 1 h 30 min. then treated with di-tert-butyl dicarbonate (17.81 g, 81.6 mmol) in dichloromethane (25 ml). The reaction mixture was stirred at 0° C. for 15 min., allowed to warm to room temperature over 30 min. then stirred overnight (20 h). The mixture was concentrated in vacuo and the residue purified by flash chromatography, eluting with 1:3 then 1:2 ethyl acetate-isohexane, to give the title compound (7.78 g, 45%) as an pale amber oil; δH (400 MHz, CDCl3) 1.47 (9H, s), 1.93-2.04 (1H, m), 2.14-2.31 (3H, m), 2.37-2.47 (2H, m), 2.80 (3H, s), 4.71 (1H, br s).

Workup

stirringThe reaction mixture was stirred at 0° C. for 15 min.
temperatureto warm to room temperature over 30 min.
stirringthen stirred overnight (20 h)
concentrationThe mixture was concentrated in vacuo
customthe residue purified by flash chromatography
washeluting with 1:3

Sources & evidence

ORD record: ord-081058d59c224906a9ba365c9fe586ca
Source dataset: uspto-grants-2007_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07276607B2

Reaction notes

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