Acetic Acid → HCID 57494025, compound

HRID 888945Notes

Reaction equation

HRID 888945 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([NH:14][CH2:15][CH2:16][O:17][CH3:18])[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[S:19]1[CH:23]=[CH:22][N:21]=[C:20]1[CH:24]=O.C(O)(=O)C.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>ClCCCl.ClCCl>[C:1]([O:5][C:6]([N:8]1[CH2:9][CH2:10][CH:11]([N:14]([CH2:15][CH2:16][O:17][CH3:18])[CH2:24][C:20]2[S:19][CH:23]=[CH:22][N:21]=2)[CH2:12][CH2:13]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

7

Reactant 4

HCID 176Acetic AcidHCID 27349031,3-Thiazole-2-carbaldehydeHCID 5049666Sodium triacetoxyborohydrideHCID 43652134tert-Butyl 4-[(2-methoxyethyl)amino]piperidine-1-carboxylate

Product 1

HCID 57494025HCID 57494025, compound

Reagents, catalysts & solvents 2

HCID 111,2-DichloroethaneSolventHCID 6344DichloromethaneSolvent

Procedure

To a mixture of 4-(2-methoxy-ethylamino)-piperidine-1-carboxylic acid tert-butyl ester (465 mg), and 2-thiazolecarboxaldehyde (190 μl) stirring in anhydrous 1,2-dichloroethane (5 ml) was added glacial acetic acid (1 equiv.) and sodium triacetoxyborohydride (458 mg). The reaction mixture was stirred for 12 hours at room temperature, then diluted with dichloromethane (40 ml), washed with brine, dried (MgSO4) and the solvents removed in vacuo. The residue was purified using flash silica chromatography to give 4[(2-methoxy-ethyl)-thiazol-2-ylmethyl-amino]-piperidine-1-carboxylic acid tert-butyl ester (574 mg). Treatment of this compound with HCl in dichloromethane/methanol and a basic wash with sodium hydrogen carbonate yielded (2-methoxy-ethyl)-piperidin-4-yl-thiazol-2-ylmethyl-amine.

Workup

  1. washwashed with brine
  2. dry with materialdried (MgSO4)
  3. customthe solvents removed in vacuo
  4. customThe residue was purified

Sources & evidence

ORD record
ord-91b81e0e2d4f4ab0a90905960dd6df27
Source dataset
uspto-grants-2012_08
Patent number
US08252792B2

Reaction notes

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