Benzyl(methoxymethyl)((trimethylsilyl)methyl)amine → HCID 89449684, compound

HRID 1969660Notes

Reaction equation

HRID 1969660 reaction equation
[CH2:1]([N:8]([CH2:12][Si](C)(C)C)[CH2:9]OC)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:17]([O:23][CH2:24][CH3:25])(=[O:22])/[CH:18]=[CH:19]\[CH2:20][CH3:21]>C(Cl)Cl.C(O)(C(F)(F)F)=O>[CH2:1]([N:8]1[CH2:9][C@H:19]([CH2:20][CH3:21])[C@H:18]([C:17]([O:23][CH2:24][CH3:25])=[O:22])[CH2:12]1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 2

HCID 353442Benzyl(methoxymethyl)((trimethylsilyl)methyl)amineHCID 11332473HCID 11332473, compound

Product 1

HCID 89449684HCID 89449684, compoundYield 96.1%

Reagents, catalysts & solvents 2

HCID 6422Trifluoroacetic acidCatalystHCID 6344DichloromethaneSolvent

Procedure

To a solution of N-benzyl-1-methoxy-N-((trimethylsilyl)methyl)methanamine (9.98 mL, 39.0 mmol), and (Z)-ethyl pent-2-enoate (5 g, 39.0 mmol, Preparation #RRR.1) in DCM (50 mL) was added TFA (0.030 mL, 0.390 mmol) at rt. After about 2 d, the reaction mixture was concd in vacuo to provide crude cis-ethyl 1-benzyl-4-ethylpyrrolidine-3-carboxylate (9.8 g, 96%) as an oil. LC/MS (Table 1, Method a) Rt=0.51 min; MS m/z: 262 (M+H)+.

Sources & evidence

ORD record
ord-0b7b38e61e7a4fe59d8ac3387f3bb3fc
Source dataset
uspto-grants-2013_04
Patent number
US08426411B2

Reaction notes

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