Ammonium Chloride → HCID 24992290, compound

HRID 2076368Notes

Reaction equation

HRID 2076368 reaction equation
[F:1][C:2]([F:23])([F:22])[C:3]1[C:4](=[O:21])[C@H:5]2[CH2:20][C@@:8]3([C:19]=1[C:18]1[CH:17]=[CH:16][C:15]4[NH:14][N:13]=[CH:12][C:11]=4[C:10]=1[CH2:9]3)[CH2:7][CH2:6]2.[BH4-].[Na+].[Cl-].[NH4+]>CCO>[F:22][C:2]([F:1])([F:23])[C:3]1[C@H:4]([OH:21])[C@H:5]2[CH2:20][C@@:8]3([C:19]=1[C:18]1[CH:17]=[CH:16][C:15]4[NH:14][N:13]=[CH:12][C:11]=4[C:10]=1[CH2:9]3)[CH2:7][CH2:6]2

Participants

5

Reactant 3

HCID 25517Ammonium ChlorideHCID 4311764Sodium borohydrideHCID 24996754HCID 24996754, compound

Product 1

HCID 24992290HCID 24992290, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a stirring solution of (8R,10aS)-6-(trifluoromethyl)-3,9,10,11-tetrahydro-8,10a-methanoazuleno[2,1-e]indazol-7(8H)-one (14 mg, 0.044 mmol) in EtOH (1 mL) was added sodium borohydride (6.7 mg, 0.18 mmol). The reaction mixture was stirred at room temperature for 1 hour after which saturated aqueous ammonium chloride was added in portions until bubbling stopped. The reaction mixture was then diluted with dichloromethane, dried over magnesium sulfate and filtered through a small pad of silica gel washing with ethyl acetate. The filtrate was concentrated under vacuum and the residue was purified by preparative TLC on silica gel (elution with 1:1 EtOAc/hexane) to give (7R,8R,10aS)-6-(trifluoromethyl)-3,7,8,9,10,11-hexahydro-8,10a-methanoazuleno[2,1-e]indazol-7-ol.

Workup

  1. additionwas added in portions
  2. customuntil bubbling
  3. additionThe reaction mixture was then diluted with dichloromethane
  4. dry with materialdried over magnesium sulfate
  5. filtrationfiltered through a small pad of silica gel washing with ethyl acetate
  6. concentrationThe filtrate was concentrated under vacuum
  7. customthe residue was purified by preparative TLC on silica gel (elution with 1:1 EtOAc/hexane)

Sources & evidence

ORD record
ord-0cc1fc74c7524384a6de3080e18debd2
Source dataset
uspto-grants-2011_04
Patent number
US07923568B2

Reaction notes

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