Sodium Sulfate → 1-(2-(Trimethylsilyl)ethyl) 1'-tert-butyl 5-(3-hydroxy-2-(hydroxymethyl)propyl)spiro[indoline-3,3'-pyrrolidine]-1,1'-dicarboxylate

HRID 1411312Notes

Reaction equation

HRID 1411312 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].C([O:9][C:10](=O)[CH:11]([C:42](OCC)=[O:43])[CH2:12][C:13]1[CH:14]=[C:15]2[C:21]3([CH2:25][CH2:24][N:23]([C:26]([O:28][C:29]([CH3:32])([CH3:31])[CH3:30])=[O:27])[CH2:22]3)[CH2:20][N:19]([C:33]([O:35][CH2:36][CH2:37][Si:38]([CH3:41])([CH3:40])[CH3:39])=[O:34])[C:16]2=[CH:17][CH:18]=1)C.S([O-])([O-])(=O)=O.[Na+].[Na+]>C(OCC)C>[OH:43][CH2:42][CH:11]([CH2:10][OH:9])[CH2:12][C:13]1[CH:14]=[C:15]2[C:21]3([CH2:25][CH2:24][N:23]([C:26]([O:28][C:29]([CH3:31])([CH3:32])[CH3:30])=[O:27])[CH2:22]3)[CH2:20][N:19]([C:33]([O:35][CH2:36][CH2:37][Si:38]([CH3:40])([CH3:39])[CH3:41])=[O:34])[C:16]2=[CH:17][CH:18]=1

Participants

5

Reactant 3

HCID 24436Sodium SulfateHCID 21226445Aluminium lithium hydrideHCID 904497891-(2-(Trimethylsilyl)ethyl) 1'-tert-butyl 5-(3-ethoxy-2-(ethoxycarbonyl)-3-oxopropyl)spiro[indoline-3,3'-pyrrolidine]-1,1'-dicarboxylate

Product 1

HCID 904497411-(2-(Trimethylsilyl)ethyl) 1'-tert-butyl 5-(3-hydroxy-2-(hydroxymethyl)propyl)spiro[indoline-3,3'-pyrrolidine]-1,1'-dicarboxylateYield 23%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

Lithium aluminum hydride (39.0 mg, 1.03 mmol) was dissolved in diethyl ether (5 mL). Thereafter, a diethyl ether (5 mL) solution of 1-(2-(trimethylsilyl)ethyl) 1′-tert-butyl 5-(3-ethoxy-2-(ethoxycarbonyl)-3-oxopropyl)spiro[indoline-3,3′-pyrrolidine]-1,1′-dicarboxylate (300 mg, 0.51 mmol) was added to the above obtained solution under cooling on ice, and the thus obtained mixture was then stirred at the same temperature as above for 1 hour. Thereafter, a saturated aqueous solution of sodium sulfate was added to the reaction solution, and the mixed solution was then filtered through a pad of celite, followed by washing with chloroform. The filtrate was concentrated in vacuo, and the obtained residue was then purified by silica gel column chromatography (chloroform:methanol=10:1) to obtain 1-(2-(trimethylsilyl)ethyl) 1′-tert-butyl 5-(3-hydroxy-2-(hydroxymethyl)propyl)spiro[indoline-3,3′-pyrrolidine]-1,1′-dicarboxylate (58.7 mg, 23%) in the form of a light red amorphous product.

Workup

  1. temperatureunder cooling on ice
  2. filtrationthe mixed solution was then filtered through a pad of celite
  3. washby washing with chloroform
  4. concentrationThe filtrate was concentrated in vacuo
  5. customthe obtained residue was then purified by silica gel column chromatography (chloroform:methanol=10:1)

Sources & evidence

ORD record
ord-7538b8becf5e4881afbc81787e4863ec
Source dataset
uspto-grants-2014_12
Patent number
US08921576B2

Reaction notes

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