Acetyl chloride → 1-[5-Bromo-2-(1-(tert-butoxycarbonyl)-4-piperidinyloxy)-phenyl]-3-trimethylsilyoxy-2-aza-1,3-butadiene

HRID 1095071Notes

Reaction equation

HRID 1095071 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([O:14][C:15]2[CH:20]=[CH:19][C:18]([Br:21])=[CH:17][C:16]=2C=O)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].C(O[C:29]([N:31]1CCC(COC2C=CC(I)=CC=2C=O)[CH2:33][CH2:32]1)=O)(C)(C)C.[CH3:48][Si:49](N[Si](C)(C)C)([CH3:51])[CH3:50].C([Li])CCC.C[Si](Cl)(C)C.C(N(CC)CC)C.C(Cl)(=[O:76])C>>[Br:21][C:18]1[CH:19]=[CH:20][C:15]([O:14][CH:11]2[CH2:10][CH2:9][N:8]([C:6]([O:5][C:1]([CH3:3])([CH3:4])[CH3:2])=[O:7])[CH2:13][CH2:12]2)=[C:16]([CH:29]=[N:31][C:32]([O:76][Si:49]([CH3:51])([CH3:50])[CH3:48])=[CH2:33])[CH:17]=1

Participants

8

Reactant 7

HCID 6367Acetyl chlorideHCID 6397ChlorotrimethylsilaneHCID 8471TriethylamineHCID 13838HexamethyldisilazaneHCID 577431634-(2-Formyl-4-iodo-phenoxymethyl)-piperidine-1-carboxylic acid tert-butyl esterHCID 594280644-(4-Bromo-2-formyl-phenoxy)-piperidine-1-carboxylic acid tert-butyl esterHCID 178418339Butyllithium

Product 1

HCID 666415371-[5-Bromo-2-(1-(tert-butoxycarbonyl)-4-piperidinyloxy)-phenyl]-3-trimethylsilyoxy-2-aza-1,3-butadiene

Procedure

In a manner similar to the method described in example 1d, 4-(4-bromo-2-formyl-phenoxy)-piperidine-1-carboxylic acid tert-butyl ester (5.5 g, 14.3 mmol) prepared in Example 15a was used as the starting material in place of 4-(2-formyl-4-iodo-phenoxymethyl)-piperidine-1-carboxylic acid tert-butyl ester to react with 1,1,3,3,3-hexamethyldisilazane (3.97 mL, 14.3 mmol), n-butyllithium (2.5 M, 5.7 mL, 14.3 mmol), trimethylsilyl chloride (1.81 mL, 14.3 mmol), triethylamine (2.59 mL, 18.6 mmol) and acetyl chloride (1.31 mL, 18.6 mmol) to give crude 1-[5-bromo-2-(1-(tert-butoxycarbonyl)-4-piperidinyloxy)-phenyl]-3-trimethylsilyoxy-2-aza-1,3-butadiene as a yellow gum and used for the next step without further purification.

Sources & evidence

ORD record
ord-f0fa10648aff47a78873d33427c148ba
Source dataset
uspto-grants-2012_03
Patent number
US08134001B2

Reaction notes

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