Isopropanol → HCID 70592898, compound

HRID 224613Notes

Reaction equation

HRID 224613 reaction equation
[CH2:1]([O:8][C:9]1[CH:34]=[CH:33][C:12]([C:13]([CH:15]([N:17]2[CH2:22][CH2:21][C:20]3([C:30]4[C:25](=[CH:26][CH:27]=[CH:28][CH:29]=4)[N:24]([CH3:31])[C:23]3=[O:32])[CH2:19][CH2:18]2)[CH3:16])=[O:14])=[CH:11][CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[BH4-].[Na+].C(O)(C)C>O>[CH2:1]([O:8][C:9]1[CH:10]=[CH:11][C:12]([CH:13]([OH:14])[CH:15]([N:17]2[CH2:18][CH2:19][C:20]3([C:30]4[C:25](=[CH:26][CH:27]=[CH:28][CH:29]=4)[N:24]([CH3:31])[C:23]3=[O:32])[CH2:21][CH2:22]2)[CH3:16])=[CH:33][CH:34]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 3776IsopropanolHCID 4311764Sodium borohydrideHCID 70594043HCID 70594043, compound

Product 1

HCID 70592898HCID 70592898, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 4.5 g of 1'-[1-(4-benzyloxybenzoyl)ethyl]-1-methyl-2-oxo-indoline-3-spiro-4'-piperidine, 5.6 g of sodium borohydride and 150 ml of isopropylalcohol was refluxed for 1 hour. The resulting mixture was poured into water and was extracted with ethylacetate. The extract was washed with water, dried over anhydrous sodium sulfate and concentrated in vacuo. The crude solid was recrystallized from ethanol to give 1'-[1-(4-benzyloxyphenyl)-1-hydroxypropane-2-yl]-1-methyl-2-oxo-indoline-3-spiro-4'-piperidine.

Workup

  1. temperaturewas refluxed for 1 hour
  2. extractionwas extracted with ethylacetate
  3. washThe extract was washed with water
  4. dry with materialdried over anhydrous sodium sulfate
  5. concentrationconcentrated in vacuo
  6. customThe crude solid was recrystallized from ethanol

Sources & evidence

ORD record
ord-a8e58e244847404c9b23498cfa32503f
Source dataset
uspto-grants-1980_11
Patent number
US04233307

Reaction notes

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