Tetrahydrofuran → HCID 58299624, compound

HRID 79225Notes

Reaction equation

HRID 79225 reaction equation
[H-].[H-].[H-].[H-].[Li+].[Al+3].C1COCC1.[C:12]1([CH2:18][N:19]2[CH2:30][CH2:29][C:22]3([NH:27][C:26](=O)[CH2:25][O:24][CH2:23]3)[CH2:21][CH2:20]2)[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1.[OH-].[Na+]>O>[C:12]1([CH2:18][N:19]2[CH2:30][CH2:29][C:22]3([NH:27][CH2:26][CH2:25][O:24][CH2:23]3)[CH2:21][CH2:20]2)[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1

Participants

6

Reactant 4

HCID 8028TetrahydrofuranHCID 14798Sodium HydroxideHCID 21226445Aluminium lithium hydrideHCID 58300057HCID 58300057, compound

Product 1

HCID 58299624HCID 58299624, compoundYield 88%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

LAH (2.00 g, 52.7 mmol) was added to a THF (100 mL) solution containing 9-(phenylmethyl)-4-oxa-1,9-diazaspiro[5.5]undecan-2-one (3.1893 g, 12.3 mmol). The resulting mixture was stirred 1 h at reflux. The reaction was then cooled to room temperature and the following additions were made slowly: 2 mL of water followed by 2 mL of 1 N NaOH, and finally 4 mL of water. The mixture was then filtered and concentrated to give a thick clear oil (2.66 g, 88% yield). The material was used in the next step without further purification. LCMS-ESI (POS), M/Z, M+1: Found 247, Calculated 247.

Workup

  1. temperatureat reflux
  2. filtrationThe mixture was then filtered
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-72e9a0fcbe8a40278954c8d4305cd05c
Source dataset
uspto-grants-2014_09
Patent number
US08841312B2

Reaction notes

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