Methanol → HCID 178453905, compound

HRID 1714389Notes

Reaction equation

HRID 1714389 reaction equation
[F:1][C:2]1[CH:14]=[CH:13][C:5]([O:6][CH:7]2[CH2:12][CH2:11][NH:10][CH2:9][CH2:8]2)=[CH:4][CH:3]=1.[C:15]([O:19][C:20](=[O:31])[NH:21][C@H:22]1[CH2:27][CH2:26][C@H:25]([CH2:28][CH:29]=O)[CH2:24][CH2:23]1)([CH3:18])([CH3:17])[CH3:16].CO.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>ClCCCl>[C:15]([O:19][C:20](=[O:31])[NH:21][C@H:22]1[CH2:23][CH2:24][C@H:25]([CH2:28][CH2:29][N:10]2[CH2:9][CH2:8][CH:7]([O:6][C:5]3[CH:13]=[CH:14][C:2]([F:1])=[CH:3][CH:4]=3)[CH2:12][CH2:11]2)[CH2:26][CH2:27]1)([CH3:18])([CH3:17])[CH3:16]

Participants

6

Reactant 4

HCID 887MethanolHCID 37348964-(4-Fluorophenoxy)piperidineHCID 5049666Sodium triacetoxyborohydrideHCID 178453924HCID 178453924, compound

Product 1

HCID 178453905HCID 178453905, compoundYield 93.8%

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

A mixture of 4-(4-fluorophenoxy)piperidine (0.150 g, 0.485 mmol), trans-[4-(2-oxo-ethyl)-cyclohexyl]-carbamic acid tert-butyl ester (0.117 g, 0.48 mmol), in 1, 2 dichloroethane (3 mL) and methanol (0.500 mL) was stirred for 4 hours at room temperature. Sodium triacetoxyborohydride (0.175 g, 0.829 mmol) was added 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/CH3OH (1-9:1). The product fractions were concentrated to give 0.176 g (0.45 mmol, 92.5% yield) of a light yellow solid. MS (m/e): 393.4 (M+H+).

Workup

  1. customcompletion of the reaction
  2. filtrationThe mixture was filtrated
  3. concentrationconcentrated to dryness
  4. custompurified with column chromatography on silica gel
  5. concentrationThe product fractions were concentrated

Sources & evidence

ORD record
ord-7ce1a7bf9f724a53a9d4185deaf370c6
Source dataset
uspto-grants-2010_09
Patent number
US07795437B2

Reaction notes

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