Ethanol → HCID 24992290, compound

HRID 2076381Notes

Reaction equation

HRID 2076381 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([CH2:19][C:18]4[C:14]5N=C[NH:17][C:13]=5[CH:12]=[CH:11][C:10]=4[C:9]=13)[CH2:7][CH2:6]2.[BH4-].[Na+].[Cl-].[NH4+:27].[CH3:28]CO>>[F:1][C:2]([F:23])([F:22])[C:3]1[C@H:4]([OH:21])[C@H:5]2[CH2:20][C@@:8]3([C:9]=1[C:10]1[CH:11]=[CH:12][C:13]4[NH:17][N:27]=[CH:28][C:14]=4[C:18]=1[CH2:19]3)[CH2:7][CH2:6]2

Participants

5

Reactant 4

HCID 702EthanolHCID 25517Ammonium ChlorideHCID 4311764Sodium borohydrideHCID 67110521HCID 67110521, compound

Product 1

HCID 24992290HCID 24992290, compound

Procedure

To a stirring solution of (8R,10aS)-6-(trifluoromethyl)-3,9,10,11-tetrahydro-8,10a-methanocyclohepta[1,2]indeno[4,5-d]imidazol-7(8H)-one (5.0 mg, 0.016 mmol) in EtOH (0.5 mL) was added sodium borohydride (2 mg, 0.05 mmol). The reaction mixture was stirred at room temperature for 0.5 hour and then saturated aqueous ammonium chloride was added. The reaction mixture was filtered through a pad of sodium sulfate on top of silica gel, washing with ethyl acetate. The filtrate was concentrated under vacuum and the residue was lyophilized from benzene containing a small amount of methanol 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. filtrationThe reaction mixture was filtered through a pad of sodium sulfate on top of silica gel
  2. washwashing with ethyl acetate
  3. concentrationThe filtrate was concentrated under vacuum

Sources & evidence

ORD record
ord-a609c16c74ab47889e40b3de86ea6e12
Source dataset
uspto-grants-2011_04
Patent number
US07923568B2

Reaction notes

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