Triethylamine → HCID 86589091, compound

HRID 1168893Notes

Reaction equation

HRID 1168893 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([CH2:14][N:15]([CH:19]2[CH2:28][CH2:27][C:26]3[C:21](=[CH:22][C:23]([OH:29])=[CH:24][CH:25]=3)[CH2:20]2)[CH2:16][CH2:17][CH3:18])[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].C(N(CC)CC)C.[CH3:37][C:38]1[C:42]([S:43](Cl)(=[O:45])=[O:44])=[C:41]([CH3:47])[O:40][N:39]=1>C(Cl)Cl>[C:1]([O:5][C:6]([N:8]1[CH2:9][CH2:10][CH:11]([CH2:14][N:15]([CH:19]2[CH2:28][CH2:27][C:26]3[C:21](=[CH:22][C:23]([O:29][S:43]([C:42]4[C:38]([CH3:37])=[N:39][O:40][C:41]=4[CH3:47])(=[O:45])=[O:44])=[CH:24][CH:25]=3)[CH2:20]2)[CH2:16][CH2:17][CH3:18])[CH2:12][CH2:13]1)=[O:7])([CH3:2])([CH3:3])[CH3:4]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 27363193,5-Dimethylisoxazole-4-sulfonyl chlorideHCID 686243534-{[(7-Hydroxy-1,2,3,4-tetrahydro-naphthalen-2-yl)-propyl-amino]-methyl}-piperidine-1-carboxylic acid tert-butyl ester

Product 1

HCID 86589091HCID 86589091, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To an ice-cold solution of 4-{[(7-hydroxy-1,2,3,4-tetrahydro-naphthalen-2-yl)-propyl-amino]-methyl}-piperidine-1-carboxylic acid tert-butyl ester, prepared as described in Example 8, (1.0 g, 2.48 mmol) and triethylamine (0.52 mL, 2.73 mmol) in methylene chloride (75 mL) under an inert atmosphere 3,5-dimethyl-isoxazole-4-sulfonyl chloride (535 mg, 2.73 mmol) was added dropwise. The reaction was allowed to warm to room temperature and stirred for 24 h. The reaction was quenched with water and the methylene chloride layer was separated, dried (MgSO4), and concentrated to afford 4-({[7-(3,5-dimethyl-isoxazole-4-sulfonyloxy)-1,2,3,4-tetrahydro-naphthalen-2-yl]-propyl-amino}-methyl)-piperidine-1-carboxylic acid tert-butyl ester (1.16 g).

Workup

  1. additionwas added dropwise
  2. customThe reaction was quenched with water
  3. customthe methylene chloride layer was separated
  4. dry with materialdried (MgSO4)
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-7e082beb631a471db59997032827488e
Source dataset
uspto-grants-2003_09
Patent number
US06627644B2

Reaction notes

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