Water → 2,3-Dihydrospiro[1H-indene-1,3′-pyrrolidin]-3-ol

HRID 1076884Notes

Reaction equation

HRID 1076884 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].[NH:7]1[C:11](=O)[CH2:10][C:9]2([C:20]3[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=3)[C:14](=[O:21])[CH2:13]2)[CH2:8]1.O>O1CCCC1.C1C=CC=CC=1>[NH:7]1[CH2:11][CH2:10][C:9]2([C:20]3[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=3)[CH:14]([OH:21])[CH2:13]2)[CH2:8]1

Participants

6

Reactant 3

HCID 962WaterHCID 12562993HCID 12562993, compoundHCID 21226445Aluminium lithium hydride

Product 1

HCID 215386612,3-Dihydrospiro[1H-indene-1,3′-pyrrolidin]-3-ol

Reagents, catalysts & solvents 2

HCID 241BenzeneSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

17.1 g of lithium aluminium hydride in 300 cc of absolute tetrahydrofuran and 600 cc of absolute benzene are placed in a Soxhlet apparatus. 30 g of the spiro[indan-1,3'-pyrrolidin]-3,5'-dione to be reduced are placed in the Soxhlet apparatus in a Soxhlet capsule. Boiling at reflux is then effected for 20 hours, whereby the entire product is dissolved. The reaction mixture is subsequently cooled and carefully decomposed with 25 cc of water in 25 cc of tetrahydrofuran, the precipitate is filtered off and the filtrate concentrated. Spiro[indan-1,3'-pyrrolidin]-3 -ol is obtained as light yellow oil and is converted into its hydrogen fumarate by reacting with a solution of 17 g of fumaric acid in 400 cc of ethanol. M.P. 155°-158° (from ethanol/ether).

Workup

  1. temperatureBoiling at reflux
  2. dissolutionwhereby the entire product is dissolved
  3. temperatureThe reaction mixture is subsequently cooled
  4. filtrationthe precipitate is filtered off
  5. concentrationthe filtrate concentrated

Sources & evidence

ORD record
ord-2e5d0d5ac4d149b982b49804bb8d7688
Source dataset
uspto-grants-1976_05
Patent number
US03958003

Reaction notes

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