Trifluoroacetic acid → HCID 64158347, compound

HRID 2274159Notes

Reaction equation

HRID 2274159 reaction equation
O[CH:2]([C:16]1[CH:20]=[CH:19][S:18][CH:17]=1)[CH:3]1[CH2:8][CH2:7][CH2:6][N:5](C(OC(C)(C)C)=O)[CH2:4]1.FC(F)(F)C(O)=O.C([SiH](CC)CC)C>>[S:18]1[CH:19]=[CH:20][C:16]([CH2:2][CH:3]2[CH2:8][CH2:7][CH2:6][NH:5][CH2:4]2)=[CH:17]1

Participants

4

Reactant 3

HCID 6422Trifluoroacetic acidHCID 12052TriethylsilaneHCID 682427241-Piperidinecarboxylic acid, 3-(hydroxy-3-thienylmethyl)-, 1,1-dimethylethyl ester

Product 1

HCID 64158347HCID 64158347, compoundYield 67.3%

Procedure

1.0 g (3.36 mmol) of tert-butyl 3-(hydroxythiophen-3-ylmethyl)piperidine-1-carboxylate as diastereomer mixture were stirred with 15 ml of trifluoroacetic acid at 0° C. After 15 min, 0.80 ml (5.04 mmol) of triethylsilane were added dropwise, the cold bath was removed, and the mixture was stirred at room temperature for 18 h. Conventional work-up gave 0.41 g of 3-thiophen-3-ylmethylpiperidine; HPLC/MS (M+H)+=182 as oil.

Workup

  1. customthe cold bath was removed

Sources & evidence

ORD record
ord-5cef6b29ee3645888a4135a320cbdf92
Source dataset
uspto-grants-2015_09
Patent number
US09126952B2

Reaction notes

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