Triethylamine → HCID 178453892, compound

HRID 72848

Reaction equation

HRID 72848 reaction equation
[F:1][C:2]1[CH:3]=[CH:4][C:5]2[O:9][N:8]=[C:7]([CH:10]3[CH2:15][CH2:14][NH:13][CH2:12][CH2:11]3)[C:6]=2[CH:16]=1.[C:17]([O:21][C:22](=[O:33])[NH:23][C@H:24]1[CH2:29][CH2:28][C@H:27]([CH2:30][CH:31]=O)[CH2:26][CH2:25]1)([CH3:20])([CH3:19])[CH3:18].C(N(CC)CC)C.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>ClCCCl>[C:17]([O:21][C:22](=[O:33])[NH:23][C@H:24]1[CH2:25][CH2:26][C@H:27]([CH2:30][CH2:31][N:13]2[CH2:12][CH2:11][CH:10]([C:7]3[C:6]4[CH:16]=[C:2]([F:1])[CH:3]=[CH:4][C:5]=4[O:9][N:8]=3)[CH2:15][CH2:14]2)[CH2:28][CH2:29]1)([CH3:20])([CH3:19])[CH3:18]

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 27947555-Fluoro-3-(4-piperidinyl)-1,2-benzisoxazoleHCID 5049666Sodium triacetoxyborohydrideHCID 178453924HCID 178453924, compound2×

Product 1

HCID 178453892HCID 178453892, compoundYield 102%

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

A mixture of 5-fluoro-3-(4-piperidinyl)-1,2-benzisoxazole (1.3 g, 5 mmol), trans-[4-(2-oxo-ethyl)-cyclohexyl]-carbamic acid tert-butyl ester (example 1, intermediate C) (1.6 g, 6 mmol), triethylamine (0.64 mL, 5 mmol) in 1,2 dichloroethane (27 mL) was stirred for 4 h at room temperature and sodium triacetoxyborohydride (1.9 g, 9 mmol) was added slowly and the resulting solution was stirred for 12 hours until the TLC indicated completion of the reaction. The mixture was filtrated and concentrated to dryness and purified with column chromatography on silica gel using CH2Cl2—CH2Cl2/MeOH (1-9:1). The product fractions were concentrated to give 2.3 g (5.1 mmol, 100% yield) of a off-white solid. MS (m/e): 446.3 (M+H+).

Workup

  1. stirringthe resulting solution was stirred for 12 hours until the TLC
  2. customcompletion of the reaction
  3. filtrationThe mixture was filtrated
  4. concentrationconcentrated to dryness
  5. custompurified with column chromatography on silica gel
  6. concentrationThe product fractions were concentrated

Sources & evidence

ORD record
ord-376f96ff0f514fed88ddc6e5c17bd469
Source dataset
uspto-grants-2014_09
Patent number
US08829029B2

Linked notes

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