Hydrochloric Acid → HCID 59578004, compound

HRID 2194122Notes

Reaction equation

HRID 2194122 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[S:8]([N:11]1[CH2:30][CH2:29][C:14]2([C:18](=[O:19])[N:17]([C:20]3[CH:28]=[CH:27][C:23]([C:24](O)=[O:25])=[CH:22][CH:21]=3)[CH2:16][CH2:15]2)[CH2:13][CH2:12]1)(=[O:10])=[O:9].Cl>C1COCC1>[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[S:8]([N:11]1[CH2:30][CH2:29][C:14]2([C:18](=[O:19])[N:17]([C:20]3[CH:21]=[CH:22][C:23]([CH2:24][OH:25])=[CH:27][CH:28]=3)[CH2:16][CH2:15]2)[CH2:13][CH2:12]1)(=[O:10])=[O:9]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 66787714HCID 66787714, compound

Product 1

HCID 59578004HCID 59578004, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

4-[8-(2-Chloro-benzenesulfonyl)-1-oxo-2,8-diaza-spiro[4.5]dec-2-yl]-benzoic acid (0.5 g) was dissolved in THF under an argon atmosphere and then treated at 0° C. with borane THF complex (1 molar, 6.68 ml) and stirred overnight at RT. Then 1M aqueous HCl (1 ml) was added and the mixture was stirred for 10 minutes. The solvent was evaporated off in vacuo, the residue was adsorbed on silica gel and chromatographed over silica gel (AcOEt/heptane, gradient from 0 to 50%) to give the desired 8-(2-chloro-benzenesulfonyl)-2-(4-hydroxymethyl-phenyl)-2,8-diaza-spiro[4.5]decan-1-one as a white solid. MS (ESI): 435.3 (MH+).

Workup

  1. additiontreated at 0° C. with borane THF complex (1 molar, 6.68 ml)
  2. stirringthe mixture was stirred for 10 minutes
  3. customThe solvent was evaporated off in vacuo
  4. customchromatographed over silica gel (AcOEt/heptane, gradient from 0 to 50%)

Sources & evidence

ORD record
ord-c842e9210a24457d944db6f043a8cb3f
Source dataset
uspto-grants-2012_12
Patent number
US08329904B2

Reaction notes

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