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

HRID 79232

Reaction equation

HRID 79232 reaction equation
[CH2:1]([N:8]1[CH2:18][CH2:17][C:11]2([O:16][CH2:15][CH2:14][NH:13][CH2:12]2)[CH2:10][CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(=O)(O)[O-].[Na+].Cl[C:25]([O:27][CH2:28][CH:29]1[C:41]2[CH:40]=[CH:39][CH:38]=[CH:37][C:36]=2[C:35]2[C:30]1=[CH:31][CH:32]=[CH:33][CH:34]=2)=[O:26].Cl>O1CCOCC1.O>[CH:40]1[C:41]2[CH:29]([CH2:28][O:27][C:25]([N:13]3[CH2:12][C:11]4([CH2:10][CH2:9][N:8]([CH2:1][C:2]5[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=5)[CH2:18][CH2:17]4)[O:16][CH2:15][CH2:14]3)=[O:26])[C:30]3[C:35](=[CH:34][CH:33]=[CH:32][CH:31]=3)[C:36]=2[CH:37]=[CH:38][CH:39]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 343679-Fluorenylmethyl chloroformateHCID 516892Sodium BicarbonateHCID 357537449-Benzyl-1-oxa-4,9-diazaspiro[5.5]undecane

Product 1

HCID 582996729H-fluoren-9-ylmethyl-9-(phenylmethyl)-1-oxa-4,9-diazaspiro[5,5]undecane-4-carboxylateYield 22.5%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Procedure

To a solution of compound 402 (2.81 g, 11.4 mmol) in 1,4-dioxane (53 mL) was added 10% sodium bicarbonate in water (21.5 mL) followed by 9-fluorenylmethyl chloroformate (2.96 g, 11.4 mmol). The resulting mixture was stirred at room temperature for four hours, and then neutralized with 3N HCl. The solution was concentrated to a solid and then purified by flash chromatography (0-10% methanol in DCM with 1% NH4OH) to give compound 403 as a white solid (1.2 g, 22.5%). LCMS-ESI (POS), M/Z, M+1: Found 469.1, Calculated 469.2.

Workup

  1. concentrationThe solution was concentrated to a solid
  2. custompurified by flash chromatography (0-10% methanol in DCM with 1% NH4OH)

Sources & evidence

ORD record
ord-e4aed5e765d545368ec3d43d3eca92f9
Source dataset
uspto-grants-2014_09
Patent number
US08841312B2

Linked notes

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