tert-Butyl piperazine-1-carboxylate → HCID 59463164, compound

HRID 1712942Notes

Reaction equation

HRID 1712942 reaction equation
[CH:1]([C:3]1[S:7][C:6]([C:8]([OH:10])=[O:9])=[CH:5][CH:4]=1)=O.[N:11]1([C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18])[CH2:16][CH2:15][NH:14][CH2:13][CH2:12]1.C([BH3-])#N.[Na+]>CO.C(O)(=O)C>[C:20]([O:19][C:17]([N:11]1[CH2:16][CH2:15][N:14]([CH2:1][C:3]2[S:7][C:6]([C:8]([OH:10])=[O:9])=[CH:5][CH:4]=2)[CH2:13][CH2:12]1)=[O:18])([CH3:23])([CH3:21])[CH3:22]

Participants

6

Reactant 3

HCID 143452tert-Butyl piperazine-1-carboxylateHCID 8188825-Formyl-2-thiophenecarboxylic AcidHCID 5003444Sodium cyanoborohydride

Product 1

HCID 59463164HCID 59463164, compoundYield 194.1%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 887MethanolSolvent

Procedure

To a solution of 5-formylthiophene-2-carboxylic acid (0.505 g, 3.23 mmol) in MeOH (35 mL) and acetic acid (0.30 mL) was added tert-butyl piperazine-1-carboxylate (1.20 g, 6.47 mmol) and sodium cyanoborohydride (0.406 g, 6.47 mmol). The reaction mixture was allowed to stir at rt for 15 h and was then concentrated to give 5-{[4-(tert-butoxycarbonyl)piperazin-1-yl]methyl}thiophene-2-carboxylic acid (2.05 g, 6.27 mmol) as a white solid. LCMS: (FA) ES+ 327.3, ES-325.4.

Workup

  1. concentrationwas then concentrated

Sources & evidence

ORD record
ord-058af110b00349b887d09117fe8eed8b
Source dataset
uspto-grants-2010_09
Patent number
US07795249B2

Reaction notes

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