Hydrochloric Acid → HCID 18378986, compound

HRID 989054Notes

Reaction equation

HRID 989054 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 3N 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).

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-a17a31705a8d4d8aa9488ef3422bb35a
Source dataset
uspto-grants-2003_10
Patent number
US06638942B1

Reaction notes

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