HCID 10736665, compound → HCID 10899439, compound

HRID 1595138Notes

Reaction equation

HRID 1595138 reaction equation
C(N1[C@@:13]2([CH2:17][CH2:16][C@@H:15]([O:18][CH2:19][C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=3)[CH2:14]2)[O:12]C[C@H]1C)(=O)C1C=CC=CC=1>CC#N>[CH2:19]([O:18][C@@H:15]1[CH2:16][CH2:17][C:13](=[O:12])[CH2:14]1)[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1

Participants

3

Reactant 1

HCID 10736665HCID 10736665, compound

Product 1

HCID 10899439HCID 10899439, compoundYield 61%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

(3R, 5S, 7R)-4-Benzoyl-7-benzyloxy-3-methyl-1-oxa-4-azaspiro[4.4]nonane (250 mg, 0.7 mmol) were dissolved in 5 ml of CH3CN. IR 120[H+] (washed 2× with ethanol and 1× with H2O) was added to a pH of 5-6, The mixture was stirred at room temperature until starting material was no longer detectable. The reaction mixture was filtered and the filtrate was concentrated on a rotary evaporator. After column chromatography, (R)-3-benzyloxycyclopentanone (81 mg, 0.4 mmol) was obtained.

Workup

  1. additionIR 120[H+] (washed 2× with ethanol and 1× with H2O) was added to a pH of 5-6
  2. filtrationThe reaction mixture was filtered
  3. concentrationthe filtrate was concentrated on a rotary evaporator

Sources & evidence

ORD record
ord-6c04090a4a644d8eb39ab543384007d2
Source dataset
uspto-grants-2001_09
Patent number
US06287829B1

Reaction notes

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