1,4-Dioxane hydrochloride → 3,3-Difluoro-1,6-diaza-spiro[3.5]nonane-1-carboxylic acid benzyl ester

HRID 1912420Notes

Reaction equation

HRID 1912420 reaction equation
C(OC([N:8]1[CH2:28][CH2:27][CH2:26][C:10]2([N:13]([C:14]([O:16][CH2:17][C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=3)=[O:15])[CH2:12][C:11]2([F:25])[F:24])[CH2:9]1)=O)(C)(C)C.Cl.O1CCOCC1>>[CH2:17]([O:16][C:14]([N:13]1[C:10]2([CH2:26][CH2:27][CH2:28][NH:8][CH2:9]2)[C:11]([F:25])([F:24])[CH2:12]1)=[O:15])[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1

Participants

3

Reactant 2

HCID 204431481,4-Dioxane hydrochlorideHCID 582933383,3-Difluoro-1,6-diaza-spiro[3.5]nonane-1,6-dicarboxylic acid 1-benzyl ester 6-tert-butyl ester

Product 1

HCID 582933343,3-Difluoro-1,6-diaza-spiro[3.5]nonane-1-carboxylic acid benzyl esterYield 118.9%

Procedure

To an optically-active compound of 3,3-difluoro-1,6-diaza-spiro[3.5]nonane-1,6-dicarboxylic acid 1-benzyl ester 6-tert-butyl ester (12.6 g) was added 4M hydrochloric acid-1,4-dioxane (126 ml), and the mixture was stirred at room temperature for 30 minutes. The mixture was concentrated under reduced pressure, and thereto was added toluene. The mixture was concentrated under reduced pressure again to give the titled compound (11.2 g).

Workup

  1. concentrationThe mixture was concentrated under reduced pressure
  2. additionwas added toluene
  3. concentrationThe mixture was concentrated under reduced pressure again

Sources & evidence

ORD record
ord-c6e78e19a0d7407681b64adec43841b6
Source dataset
uspto-grants-2013_12
Patent number
US08609647B2

Reaction notes

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