9H-fluoren-9-ylmethyl-9-(phenylmethyl)-1-oxa-4,9-diazaspiro[5,5]undecane-4-carboxylate → 9H-fluoren-9-ylmethyl-1-oxa-4,9-diazaspiro[5.5]undecane-4-carboxylate

HRID 876056Notes

Reaction equation

HRID 876056 reaction equation
[CH:1]1[C:13]2[CH:12]([CH2:14][O:15][C:16]([N:18]3[CH2:23][C:22]4([CH2:28][CH2:27][N:26](CC5C=CC=CC=5)[CH2:25][CH2:24]4)[O:21][CH2:20][CH2:19]3)=[O:17])[C:11]3[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=3)[C:5]=2[CH:4]=[CH:3][CH:2]=1>C(O)C>[CH:10]1[C:11]2[CH:12]([CH2:14][O:15][C:16]([N:18]3[CH2:23][C:22]4([CH2:28][CH2:27][NH:26][CH2:25][CH2:24]4)[O:21][CH2:20][CH2:19]3)=[O:17])[C:13]3[C:5](=[CH:4][CH:3]=[CH:2][CH:1]=3)[C:6]=2[CH:7]=[CH:8][CH:9]=1

Participants

3

Reactant 1

HCID 582996729H-fluoren-9-ylmethyl-9-(phenylmethyl)-1-oxa-4,9-diazaspiro[5,5]undecane-4-carboxylate

Product 1

HCID 683226439H-fluoren-9-ylmethyl-1-oxa-4,9-diazaspiro[5.5]undecane-4-carboxylateYield 61.4%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of compound 403 (1.43 g, 3.05 mmol) in ethanol (27 mL) was added palladium hydroxide, 20 wt % pd (dry basis) on carbon, wet (1.51 g, 2.15 mmol), followed by hydrochloric acid (0.10 mL). The sealed glass tube was then evacuated and purged with hydrogen three times. The sealed tube was then charged with hydrogen (50 psi), and allowed to stir at room temperature for three days. HPLC showed ˜85% conversion to the desired product. After filtering the mixture through a plug of celite, the filtrate was concentrated to a solid and purified by flash chromatography (0-20% methanol in DCM with 1% NH4OH) to give compound 404 (709 mg, 61%) as a white solid. LCMS-ESI (POS), M/Z, M+1: Found 379.1, Calculated 379.2.

Workup

  1. dry with materialpalladium hydroxide, 20 wt % pd (dry basis) on carbon, wet (1.51 g, 2.15 mmol)
  2. customThe sealed glass tube was then evacuated
  3. custompurged with hydrogen three times
  4. additionThe sealed tube was then charged with hydrogen (50 psi)
  5. filtrationAfter filtering the mixture through a plug of celite
  6. concentrationthe filtrate was concentrated to a solid
  7. custompurified by flash chromatography (0-20% methanol in DCM with 1% NH4OH)

Sources & evidence

ORD record
ord-75ef7ed4c1364084b509c29959fd8f00
Source dataset
uspto-grants-2015_03
Patent number
US08980903B2

Reaction notes

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