Oxalic Acid → HCID 178461428, compound

HRID 657672Notes

Reaction equation

HRID 657672 reaction equation
[O:1]=[C:2]1[CH2:7][CH2:6][CH:5]([C:8]2[CH:24]=[CH:23][C:11]([O:12][CH2:13][CH2:14][CH2:15][N:16]3[CH2:21][CH2:20][CH2:19][C@H:18]([CH3:22])[CH2:17]3)=[CH:10][CH:9]=2)[CH2:4][CH2:3]1.[BH4-].[Na+].C([O-])(=O)C([O-])=O.C(O)(=O)C(O)=O>CO.C(O)C.C(OCC)C>[OH:1][C@H:2]1[CH2:7][CH2:6][C@H:5]([C:8]2[CH:24]=[CH:23][C:11]([O:12][CH2:13][CH2:14][CH2:15][N:16]3[CH2:21][CH2:20][CH2:19][C@H:18]([CH3:22])[CH2:17]3)=[CH:10][CH:9]=2)[CH2:4][CH2:3]1

Participants

8

Reactant 4

HCID 971Oxalic AcidHCID 71081Oxalate2×HCID 4311764Sodium borohydrideHCID 57672031HCID 57672031, compound

Product 1

HCID 178461428HCID 178461428, compoundYield 19.3%

Reagents, catalysts & solvents 3

HCID 702EthanolSolventHCID 887MethanolSolventHCID 3283Diethyl EtherSolvent

Procedure

A To a solution of (3S)-1-{3-[4-(4-oxocyclohexyl)phenoxy]propyl}-3-methylpiperidine (170 mg) in methanol (5 mL) is added sodium borohydride (20 mg). The mixture is stirred for one hour at room temperature, and then concentrated under reduced pressure. The residue is partitioned between water (5 mL) and ethyl acetate (10 mL). The aqueous phase is extracted twice with ethyl acetate. The organic extracts are pooled, dried over magnesium sulfate, concentrated under reduced pressure to give 129 mg of crude base which is converted to the oxalate with oxalic acid (35 mg) in a mixture of ethanol and diethyl ether, giving 33 mg of (3S)-1-{3-[trans-4-(4-hydroxycyclohexyl)phenoxy]propyl}-3-methylpiperidine, oxalate as a white powder.

Workup

  1. concentrationconcentrated under reduced pressure
  2. customThe residue is partitioned between water (5 mL) and ethyl acetate (10 mL)
  3. extractionThe aqueous phase is extracted twice with ethyl acetate
  4. dry with materialdried over magnesium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customto give 129 mg of crude base which

Sources & evidence

ORD record
ord-fbb6f5136c484dbf80c1a0b3f5511541
Source dataset
uspto-grants-2011_12
Patent number
US08076329B2

Reaction notes

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