Sodium borohydride → HCID 67110511, compound

HRID 2076369Notes

Reaction equation

HRID 2076369 reaction equation
[Cl:1][C:2]1[C:3](=[O:30])[C@H:4]2[CH2:29][C@@:7]3([C:18]=1[C:17]1[CH:16]=[CH:15][C:14]4[N:13]([S:19]([C:22]5[CH:27]=[CH:26][C:25]([CH3:28])=[CH:24][CH:23]=5)(=[O:21])=[O:20])[N:12]=[CH:11][C:10]=4[C:9]=1[CH2:8]3)[CH2:6][CH2:5]2.[Cl:31][C:32]1[C:33](=[O:60])[C@H:34]2[CH2:59][C@@:37]3([C:48]=1[C:47]1[CH:46]=[CH:45][C:44]4[C:40](=[CH:41][N:42]([S:49]([C:52]5[CH:57]=[CH:56][C:55]([CH3:58])=[CH:54][CH:53]=5)(=[O:51])=[O:50])[N:43]=4)[C:39]=1[CH2:38]3)[CH2:36][CH2:35]2.[BH4-].[Na+]>C(O)C>[Cl:1][C:2]1[C@H:3]([OH:30])[C@H:4]2[CH2:29][C@@:7]3([C:18]=1[C:17]1[CH:16]=[CH:15][C:14]4[N:13]([S:19]([C:22]5[CH:23]=[CH:24][C:25]([CH3:28])=[CH:26][CH:27]=5)(=[O:20])=[O:21])[N:12]=[CH:11][C:10]=4[C:9]=1[CH2:8]3)[CH2:6][CH2:5]2.[Cl:31][C:32]1[C@H:33]([OH:60])[C@H:34]2[CH2:59][C@@:37]3([C:48]=1[C:47]1[CH:46]=[CH:45][C:44]4[C:40](=[CH:41][N:42]([S:49]([C:52]5[CH:53]=[CH:54][C:55]([CH3:58])=[CH:56][CH:57]=5)(=[O:50])=[O:51])[N:43]=4)[C:39]=1[CH2:38]3)[CH2:36][CH2:35]2

Participants

6

Reactant 3

HCID 4311764Sodium borohydrideHCID 67110508HCID 67110508, compoundHCID 67110768HCID 67110768, compound

Product 2

HCID 67110511HCID 67110511, compoundHCID 67110704HCID 67110704, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
0 °C

Procedure

A mixture of (8R,10aS)-6-chloro-3-[(4-methylphenyl)sulfonyl]-3,9,10,11-tetrahydro-8,10a-methanoazuleno[2,1-e]indazol-7(8H)-one and (8R,10aS) -6-chloro-2-[(4-methylphenyl)sulfonyl]-2,9,10,11-tetrahydro-8,10a-methanoazuleno[2,1-e]indazol-7(8H) -one prepared as described in Step 1 (0.026 g, 0.059 mmol) was dissolved in 0.5 mL of ethanol, cooled to 0° C., and sodium borohydride (0.013 g, 0.34 mmol) was added. After 30 minutes, the reaction was quenched by addition of three drops of saturated NH4Cl, diluted with dichloromethane, and dried over MgSO4. The solution was filtered through a pad of silica gel, rinsing with EtOAc, and concentrated under reduced pressure to give (7R,8R,10aS)-6-chloro-3-[(4-methylphenyl)sulfonyl]-3,7,8,9,10,11-hexahydro-8,10a-methanoazuleno[2,1-e]indazol-7-ol and (7R,8R,10aS)-6-chloro-2-[(4-methylphenyl)sulfonyl]-2,7,8,9,10,11-hexahydro-8,10a-methanoazuleno[2,1-e]indazol-7-ol.

Workup

  1. customprepared
  2. customthe reaction was quenched by addition of three drops of saturated NH4Cl
  3. additiondiluted with dichloromethane
  4. dry with materialdried over MgSO4
  5. filtrationThe solution was filtered through a pad of silica gel
  6. washrinsing with EtOAc
  7. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-c80960e83a9c4436be8ade637200126f
Source dataset
uspto-grants-2011_04
Patent number
US07923568B2

Reaction notes

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