1-(Diphenylmethyl)azetidine-3-carbonitrile → HCID 58079830, compound

HRID 1961546Notes

Reaction equation

HRID 1961546 reaction equation
[Br:1][C:2]1[CH:7]=[C:6]([CH:8]([O:12][CH2:13][CH3:14])[O:9][CH2:10][CH3:11])[CH:5]=[CH:4][C:3]=1F.[CH:16]([N:29]1[CH2:32][CH:31]([C:33]#[N:34])[CH2:30]1)([C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1)[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1.C[Si]([N-][Si](C)(C)C)(C)C.[K+]>C1COCC1>[CH:16]([N:29]1[CH2:32][C:31]([C:3]2[CH:4]=[CH:5][C:6]([CH:8]([O:12][CH2:13][CH3:14])[O:9][CH2:10][CH3:11])=[CH:7][C:2]=2[Br:1])([C:33]#[N:34])[CH2:30]1)([C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1)[C:17]1[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=1

Participants

5

Reactant 3

HCID 27792901-(Diphenylmethyl)azetidine-3-carbonitrileHCID 3251421Potassium bis(trimethylsilyl)amideHCID 131165852-Bromo-4-(diethoxymethyl)-1-fluorobenzene

Product 1

HCID 58079830HCID 58079830, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

2-bromo-4-(diethoxymethyl)-1-fluorobenzene (Preparation 31, 1 g) and 1-benzhydrylazetidine-3-carbonitrile (2.7 g) were dissolved in anhydrous THF (4 mL). KHMDS (2.2 g) was then added all at once. The solution became dark brown instantaneously. The reaction was stirred at room temperature overnight. An LC-Ms confirms complete conversion into the desired product: [433]˜3.31 minutes and [505]˜3.62 min. Both peaks correspond to desired product: one is the aldehyde, and the other is the acetal. The crude reaction mixture was concentrated to an oil, and loaded on a 80 g SiO2 cartridge, then eluted with a gradient 0-100% ethylacetate in heptane. The desired fractions were collected and concentrated in vacuum. The resulting oil was suspended in methanol and sonicated for 30 sec, and the resulting white powder is filtered and used as such in the next step. 55% yield. LC-MS [505].

Sources & evidence

ORD record
ord-7857f0704bda46329d8196f91f261c0d
Source dataset
uspto-grants-2013_04
Patent number
US08415310B2

Reaction notes

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