2-Bromo-5-methylthiophene → 4-[1-(3-Bromo-5-methyl-thiophen-2-yl)-methanoyl]-piperidine-1-carboxylic acid tert-butyl ester

HRID 501300Notes

Reaction equation

HRID 501300 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([C:14]([C:16]2[S:17][CH:18]=[C:19](C)[C:20]=2[Br:21])=[O:15])[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].Br[C:24]1SC(C)=CC=1.C([N-]C(C)C)(C)C.[Li+].CON(C)C(C1CCN(C(OC(C)(C)C)=O)CC1)=O>>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([C:14]([C:16]2[S:17][C:18]([CH3:24])=[CH:19][C:20]=2[Br:21])=[O:15])[CH2:10][CH2:9]1)=[O:7])([CH3:3])([CH3:2])[CH3:4]

Participants

5

Reactant 4

HCID 698312-Bromo-5-methylthiopheneHCID 2724682Lithium diisopropylamideHCID 11065582tert-Butyl 4-(methoxy(methyl)carbamoyl)piperidine-1-carboxylateHCID 588177114-[1-(3-Bromo-4-methyl-thiophen-2-yl)-methanoyl]-piperidine-1-carboxylic acid tert-butyl ester

Product 1

HCID 588176824-[1-(3-Bromo-5-methyl-thiophen-2-yl)-methanoyl]-piperidine-1-carboxylic acid tert-butyl ester

Procedure

Prepared essentially as in 29a except that 2-bromo-5-methyl thiophene is used as the starting material. In addition, 1.20 equivalents of lithium diisopropylamide and 1.24 equivalents of 4-(methoxy-methyl-carbamoyl)-piperidine-1-carboxylic acid. tert-butyl ester are used for the reaction. Accordingly, stirring time of the reaction mixture may vary. Purification of the residue via flash column chromatography uses a gradient with a mixture of ethyl acetate: n-heptane (1:9) to ethyl acetate: n-heptane (2:8) to yield a yellow oil. LC/MS (ESI), m/e 332 (M-56) and 388 (MH+), retention time 2.15 minutes. Condition II.

Workup

  1. customPurification of the residue via flash column chromatography
  2. additionwith a mixture of ethyl acetate: n-heptane (1:9) to ethyl acetate: n-heptane (2:8)
  3. customto yield a yellow oil

Sources & evidence

ORD record
ord-a6bbeb43449c476b92ad6e6087162484
Source dataset
uspto-grants-2010_08
Patent number
US07772252B2

Reaction notes

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