Sodium Hydroxide → HCID 69159097, compound

HRID 349765Notes

Reaction equation

HRID 349765 reaction equation
[CH3:1][S:2]([C:5]1[CH:17]=[CH:16][C:8]([O:9][CH:10]2[CH2:15][CH2:14][NH:13][CH2:12][CH2:11]2)=[CH:7][CH:6]=1)(=[O:4])=[O:3].[C:18]([N:25]1[CH2:30][CH2:29][C:28](=O)[CH2:27][CH2:26]1)([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19].[BH-](OC(C)=O)(OC(C)=O)OC(C)=O.[Na+].[OH-].[Na+]>C1COCC1.ClCCl.C(O)(=O)C.ClCCCl>[C:21]([O:20][C:18]([N:25]1[CH2:30][CH2:29][CH:28]([N:13]2[CH2:14][CH2:15][CH:10]([O:9][C:8]3[CH:7]=[CH:6][C:5]([S:2]([CH3:1])(=[O:4])=[O:3])=[CH:17][CH:16]=3)[CH2:11][CH2:12]2)[CH2:27][CH2:26]1)=[O:19])([CH3:24])([CH3:22])[CH3:23]

Participants

9

Reactant 4

HCID 14798Sodium HydroxideHCID 735900tert-Butyl 4-oxopiperidine-1-carboxylateHCID 5049666Sodium triacetoxyborohydrideHCID 18538643HCID 18538643, compound

Product 1

HCID 69159097HCID 69159097, compoundYield 91.5%

Reagents, catalysts & solvents 4

HCID 111,2-DichloroethaneSolventHCID 176Acetic AcidSolventHCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 4-(4-methanesulfonyl-phenoxy)-piperidine (0.7 g) dissolved in THF (5 ml) and 1,2-dichloroethane (10 ml) with 1-Boc-4-piperidone (0.71 g) was added NaBH(OAc)3 (0.926 g) and acetic acid (0.18 g). After 16 hours at RT aqueous NaOH (1M) solution and dichloromethane were added and the mixture was extracted with dichloromethane. The combined organic extracts were washed with water, dried with magnesium sulfate and concentrated to leave a residue which was purified by chromatography (dichloromethane:methanol 90:10) to give the sub-title product (1.1 g; MS: APCI+(M+H) 439).

Workup

  1. extractionthe mixture was extracted with dichloromethane
  2. washThe combined organic extracts were washed with water
  3. dry with materialdried with magnesium sulfate
  4. concentrationconcentrated
  5. customto leave a residue which
  6. customwas purified by chromatography (dichloromethane:methanol 90:10)

Sources & evidence

ORD record
ord-8f4d3f811b8d4dcf8ed10a3d62ebfcbe
Source dataset
uspto-grants-2007_02
Patent number
US07179922B2

Reaction notes

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