Hydrochloric Acid → HCID 18378986, compound

HRID 2298960Notes

Reaction equation

HRID 2298960 reaction equation
[CH3:1][S:2]([N:5]1[C:30]2[C:25](=[CH:26][CH:27]=[CH:28][CH:29]=2)[C:7]2([CH2:12][CH2:11][N:10]([C:13]([NH:15][C:16]3[CH:21]=[CH:20][C:19](C(=O)C)=[CH:18][CH:17]=3)=[O:14])[CH2:9][CH2:8]2)[CH2:6]1)(=[O:4])=[O:3].[BH4-].[Na+].Cl.[CH2:34]([OH:36])[CH3:35].ClCCl>>[CH3:1][S:2]([N:5]1[C:30]2[C:25](=[CH:26][CH:27]=[CH:28][CH:29]=2)[C:7]2([CH2:12][CH2:11][N:10]([C:13]([NH:15][C:16]3[CH:17]=[CH:18][C:19]([CH2:35][CH2:34][OH:36])=[CH:20][CH:21]=3)=[O:14])[CH2:9][CH2:8]2)[CH2:6]1)(=[O:3])=[O:4]

Participants

5

Reactant 4

HCID 313Hydrochloric AcidHCID 4311764Sodium borohydrideHCID 18004934HCID 18004934, compoundHCID 21584144Dichloromethane ethanol

Product 1

HCID 18378986HCID 18378986, compound

Procedure

To a stirred solution of 1-methylsufonyl-N-(4-acetylphenyl)spiro[indoline-3,4′-piperidine]-1′-carboxamide (400 mg) in ethanol/dichloromethane (5/5 mL) at 0° C., was added sodium borohydride (100 mg). The mixture was stirred for 1 hour, then 3 N HCl (0.2 mL) was added to destroy the excess hydride. The mixture was then concentrated and partitioned between water and dichloromethane. The organic layer was dried over MgSO4 and evaporated to give the title compound, 1600 as white powder (386 mg). ESI-MS: 430 (M+1)

Workup

  1. customto destroy the excess hydride
  2. concentrationThe mixture was then concentrated
  3. custompartitioned between water and dichloromethane
  4. dry with materialThe organic layer was dried over MgSO4
  5. customevaporated

Sources & evidence

ORD record
ord-f3626cb47fba40449d0c73fe5af8e41e
Source dataset
uspto-grants-2002_12
Patent number
US06495559B2

Reaction notes

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