Acetic Acid → HCID 21936984, compound

HRID 746481Notes

Reaction equation

HRID 746481 reaction equation
[C:1]1([CH:7]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)[CH2:8][CH2:9][NH2:10])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].C(O)(=O)C.[C:35]([N:42]1[CH2:47][CH2:46][CH2:45][CH2:44][C:43]1=O)([O:37][C:38]([CH3:41])([CH3:40])[CH3:39])=[O:36]>ClC(Cl)C>[C:11]1([CH:7]([C:1]2[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=2)[CH2:8][CH2:9][NH:10][CH:45]2[CH2:46][CH2:47][N:42]([C:35]([O:37][C:38]([CH3:41])([CH3:40])[CH3:39])=[O:36])[CH2:43][CH2:44]2)[CH:12]=[CH:13][CH:14]=[CH:15][CH:16]=1

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 796983,3-DiphenylpropylamineHCID 5049666Sodium triacetoxyborohydrideHCID 7577838tert-Butyl 2-oxopiperidine-1-carboxylate

Product 1

HCID 21936984HCID 21936984, compoundYield 101.4%

Reagents, catalysts & solvents 1

HCID 63651,1-DichloroethaneSolvent

Procedure

3.3-diphenylpropylamine (5.8 g, 27.5 mmol), sodium triacetoxyborohydride (6.36 g, 30 mmol) and 0.5 ml of acetic acid are added to 5 g (25 mmol) of N-Boc-piperidone in 100 ml of dry dichloroethane. The turbid yellow solution is agitated at ambient temperature for 1 hour. 50 ml of a soda solution (0.1 M) is then added and the mixture is agitated for 30 minutes. The organic phase is washed with a saturated solution of sodium bicarbonate, with sodium chloride, dried over magnesium sulphate, filtered and concentrated in order to produce 10 g of a yellow solid. This solid is purified by flash chromatography on silica gel eluting with a heptane/ethyl acetate mixture (4/1, 3/1, 2/1 then 1/1) then with pure ethyl acetate. The fractions are concentrated under vacuum in order to produce 5.6 g (yield=57%) of a pale yellow solid.

Workup

  1. stirringthe mixture is agitated for 30 minutes
  2. washThe organic phase is washed with a saturated solution of sodium bicarbonate, with sodium chloride
  3. dry with materialdried over magnesium sulphate
  4. filtrationfiltered
  5. concentrationconcentrated in order

Sources & evidence

ORD record
ord-75185f3740154b7b9342a47d196a05f2
Source dataset
uspto-grants-2008_07
Patent number
US07393861B2

Reaction notes

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