Water → Spiro[cyclobutane-1,3'-indoline]

HRID 74520Notes

Reaction equation

HRID 74520 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].[NH:7]1[C:15]2[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=2)[C:9]2([CH2:18][CH2:17][CH2:16]2)[C:8]1=O.O>C1COCC1>[NH:7]1[C:15]2[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=2)[C:9]2([CH2:18][CH2:17][CH2:16]2)[CH2:8]1

Participants

5

Reactant 3

HCID 962WaterHCID 13728292Spiro[cyclobutane-1,3'-indolin]-2'-oneHCID 21226445Aluminium lithium hydride

Product 1

HCID 27274706Spiro[cyclobutane-1,3'-indoline]

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
65 °C

Procedure

Under a nitrogen atmosphere 0.60 mL (0.60 mmol) of a 1M solution of lithium aluminium hydride in THF was added dropwise to 100 mg (0.58 mmol) spiro[cyclobutan-1,3′-indolin]-2′-one in 20 mL THF. Then the reaction mixture was stirred for 1 h at 65° C. After cooling 1 mL water was added and the mixture was stirred for 10 min. The organic phase was dried on sodium sulphate and evaporated down. The product was reacted without further purification.

Workup

  1. additionwas added
  2. stirringthe mixture was stirred for 10 min
  3. customThe organic phase was dried on sodium sulphate
  4. customevaporated down
  5. customThe product was reacted without further purification

Sources & evidence

ORD record
ord-9109817342504eebb5d572e75288b5fe
Source dataset
uspto-grants-2014_09
Patent number
US08829006B2

Reaction notes

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