Acetyl chloride → (R/S)-1-[2-(1-tert-butoxycarbonyl-3-pyrrolidinyloxy)-5-iodo-phenyl]-3-trimethylsilyoxy-2-aza-1,3-butadiene

HRID 1095094Notes

Reaction equation

HRID 1095094 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:12][CH2:11][CH:10]([O:13][C:14]2[CH:19]=[CH:18][C:17]([I:20])=[CH:16][C:15]=2C=O)[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].C(O[C:28]([N:30]1CCC(COC2C=CC(I)=CC=2C=O)[CH2:32][CH2:31]1)=O)(C)(C)C.[CH3:47][Si:48](N[Si](C)(C)C)([CH3:50])[CH3:49].C([Li])CCC.C[Si](Cl)(C)C.C(N(CC)CC)C.C(Cl)(=[O:75])C>>[C:1]([O:5][C:6]([N:8]1[CH2:12][CH2:11][CH:10]([O:13][C:14]2[CH:19]=[CH:18][C:17]([I:20])=[CH:16][C:15]=2[CH:28]=[N:30][C:31]([O:75][Si:48]([CH3:50])([CH3:49])[CH3:47])=[CH2:32])[CH2:9]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

8

Reactant 7

HCID 6367Acetyl chlorideHCID 6397ChlorotrimethylsilaneHCID 8471TriethylamineHCID 13838HexamethyldisilazaneHCID 577431634-(2-Formyl-4-iodo-phenoxymethyl)-piperidine-1-carboxylic acid tert-butyl esterHCID 57743241(r/s)-3-(2-Formyl-4-iodo-phenoxy)-pyrrolidine-1-carboxylic acid tert-butyl esterHCID 178418339Butyllithium

Product 1

HCID 66641566(R/S)-1-[2-(1-tert-butoxycarbonyl-3-pyrrolidinyloxy)-5-iodo-phenyl]-3-trimethylsilyoxy-2-aza-1,3-butadiene

Procedure

In a manner similar to the method described in example 1d, (R/S)-3-(2-formyl-4-iodo-phenoxy)-pyrrolidine-1-carboxylic acid tert-butyl ester (4.2 g, 10 mmol) 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 (1.6 g, 10 mmol), n-butyllithium (2.5 M, 4 mL, 10 mmol), trimethylsilyl chloride (1.1 g, 10 mmol), triethylamine (1.36 g, 13.6 mmol) and acetyl chloride (1 g, 13.6 mmol) to give crude (R/S)-1-[2-(1-tert-butoxycarbonyl-3-pyrrolidinyloxy)-5-iodo-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-0228e57bbb484d33b68a63289eb9067a
Source dataset
uspto-grants-2012_03
Patent number
US08134001B2

Reaction notes

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