HCID 14658342, compound → HCID 14658389, compound

HRID 1199838Notes

Reaction equation

[CH2:1]([N:3]([CH2:6]/[CH:7]=[C:8](\[CH3:14])/[CH:9]([O:12][CH3:13])[O:10][CH3:11])[CH2:4][CH3:5])[CH3:2]>O1CCCC1>[CH2:1]([N:3](/[CH:6]=[CH:7]/[C@H:8]([CH3:14])[CH:9]([O:12][CH3:13])[O:10][CH3:11])[CH2:4][CH3:5])[CH3:2]

Participants

Conditions

Temperature: 90 °C

Procedure

A pyrex bomb tube was charged with 2.02 g (10 mmol) of (E)-N,N-diethyl-4,4-dimethoxy-3-methyl-2-butenylamine, 10 ml of tetrahydrofuran and 83.2 mg (0.10 mmol) of [η4 -bicyclo[2.2.1]hepta-2,5-diene][(S)-(6,6'-dimethyl-2,2'-biphenylylene)-bis(diphenylphosphine)] rhodium (I) tetrafluoroborate. After degasifying the mixture, the tube was sealed and heated at 90° C. for 56 hours in a bomb tube oven. The red-brown solution was evaporated and the residue was distilled in a bulb-tube at about 70°/0.2 mmHg. There was obtained (1E,3S)-N,N-diethyl-4,4-dimethoxy-3-methyl-1-butenylamine; purity according to gas chromatography 70%; [α]D20 =-12.9° (c=4.05% in hexane). The corresponding (S)-4,4-dimethoxy-3-methylbutanal has a rotation [α]D20 =-23.3° (c=4.66% in hexane); purity according to gas chromatography 96%.

Workup

customthe tube was sealed
customThe red-brown solution was evaporated
distillationthe residue was distilled in a bulb-tube at about 70°/0.2 mmHg

Sources & evidence

ORD record: ord-c011209865954d0baf01196144ee2b19
Source dataset: uspto-grants-1990_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04902818

Reaction notes

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