Water → HCID 69593555, compound

HRID 1790424Notes

Reaction equation

HRID 1790424 reaction equation
[C:1]([N:4]1[CH2:9][CH2:8][C@@H:7]([N:10]2[C:18]3[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=3)[CH2:12][CH2:11]2)[C@H:6]([C:19](OCC)=[O:20])[CH2:5]1)(=[O:3])[CH3:2].[BH4-].[Na+].C(OCC)(=O)C.O>C(O)C>[C:1]([N:4]1[CH2:9][CH2:8][C@@H:7]([N:10]2[C:18]3[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=3)[CH2:12][CH2:11]2)[C@H:6]([CH2:19][OH:20])[CH2:5]1)(=[O:3])[CH3:2]

Participants

6

Reactant 4

HCID 962WaterHCID 8857Ethyl AcetateHCID 4311764Sodium borohydride2×HCID 69593590HCID 69593590, compound

Product 1

HCID 69593555HCID 69593555, compoundYield 39%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of trans-1-(1-acetyl-3-ethoxycarbonyl-piperidin-4-yl)indoline (780 mg) in ethanol (40 ml) was added sodium borohydride (5.7 g) in 3 portions at 30 min. intervals. After stirring at room temperature overnight, sodium borohydride (3.3 g) was added thereto and the resultant mixture was stirred for additional 4 hr. Then ethyl acetate (20 ml) and water (50 ml) were successively added carefully to the reaction mixture followed by extraction with ethyl acetate (50 ml) for three times. The organic phase was washed with water (100 ml) twice and brine once, dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (methylene chloride/methanol system) to give the title compound (250 mg) as a yellow powder (yield: 39%).

Workup

  1. extractionfollowed by extraction with ethyl acetate (50 ml) for three times
  2. washThe organic phase was washed with water (100 ml) twice
  3. dry with materialbrine once, dried over anhydrous magnesium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was purified by silica gel column chromatography (methylene chloride/methanol system)

Sources & evidence

ORD record
ord-a6f9dfc9446d4a34ad9dc802fdee3ced
Source dataset
uspto-grants-2006_07
Patent number
US07071201B2

Reaction notes

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