Water → HCID 86589090, compound

HRID 983481Notes

Reaction equation

HRID 983481 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.[F:37][C:38]([F:44])([F:43])[S:39](Cl)(=[O:41])=[O:40].O>C(Cl)Cl>[C:1]([O:5][C:6]([N:8]1[CH2:9][CH2:10][CH:11]([CH2:14][N:15]([CH2:16][CH2:17][CH3:18])[CH:19]2[CH2:28][CH2:27][C:26]3[C:21](=[CH:22][C:23]([O:29][S:39]([C:38]([F:44])([F:43])[F:37])(=[O:41])=[O:40])=[CH:24][CH:25]=3)[CH2:20]2)[CH2:12][CH2:13]1)=[O:7])([CH3:2])([CH3:3])[CH3:4]

Participants

6

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 79000Trifluoromethanesulfonyl 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 86589090HCID 86589090, compoundYield 54.9%

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 (300 mg, 0.75 mmol) in methylene chloride (30 mL) under a nitrogen atmosphere was added triethylamine (0.16 ml, 1.125 mmol) followed by trifluoromethanesulfonyl chloride (0.08 ml, 0.78 mmol). The reaction was stirred in the ice bath for 30 min. and then added to water (60 ml). The organic layer was separated, dried over MgSO4, filtered, and concentrated. Chromatography with 40% acetone in hexanes affords 4-{[propyl-(7-trifluoromethanesulfonyloxy-1,2,3,4-tetrahydro-naphthalen-2-yl)-amino]-methyl}-piperidine-1-carboxylic acid tert-butyl ester (220 mg).

Workup

  1. customThe organic layer was separated
  2. dry with materialdried over MgSO4
  3. filtrationfiltered
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-18a75771f0c34a2b91c75f8669189cce
Source dataset
uspto-grants-2005_03
Patent number
US06864266B2

Reaction notes

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