Methanol → 1-Benzo[b]thiophen-3-yl-3-(9-naphthalen-2-yl-7,9-diaza-bicyclo[4.2.2]dec-3-en-7-yl)-propan-1-ol

HRID 40643Notes

Reaction equation

HRID 40643 reaction equation
[S:1]1[CH:5]=[C:4]([C:6](=[O:29])[CH2:7][CH2:8][N:9]2[CH2:16][CH:15]3[N:17]([C:19]4[CH:28]=[CH:27][C:26]5[C:21](=[CH:22][CH:23]=[CH:24][CH:25]=5)[CH:20]=4)[CH2:18][CH:10]2[CH2:11][CH:12]=[CH:13][CH2:14]3)[C:3]2[CH:30]=[CH:31][CH:32]=[CH:33][C:2]1=2.[BH4-].[Na+].CO.[OH-].[Na+]>C(OCC)(=O)C>[S:1]1[CH:5]=[C:4]([CH:6]([OH:29])[CH2:7][CH2:8][N:9]2[CH2:16][CH:15]3[N:17]([C:19]4[CH:28]=[CH:27][C:26]5[C:21](=[CH:22][CH:23]=[CH:24][CH:25]=5)[CH:20]=4)[CH2:18][CH:10]2[CH2:11][CH:12]=[CH:13][CH2:14]3)[C:3]2[CH:30]=[CH:31][CH:32]=[CH:33][C:2]1=2

Participants

6

Reactant 4

HCID 887MethanolHCID 14798Sodium HydroxideHCID 4311764Sodium borohydrideHCID 692332961-Benzo[b]thiophen-3-yl-3-(9-naphthalen-2-yl-7,9-diaza-bicyclo[4.2.2]dec-3-en-7-yl)-propan-1-one

Product 1

HCID 692325911-Benzo[b]thiophen-3-yl-3-(9-naphthalen-2-yl-7,9-diaza-bicyclo[4.2.2]dec-3-en-7-yl)-propan-1-ol

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

1-Benzo[b]thiophen-3-yl-3-(9-naphthalen-2-yl-7,9-diaza-bicyclo[4.2.2]dec-3-en-7-yl)-propan-1-one (8 mg, 0.0176 mmol), sodium borohydride (20 mg, 0.5 mmol) and methanol (1 ml), were placed in a round bottom flask and the reaction mixture stirred for one hour at room temperature. To the reaction mixture were then added a solution of 1N NaOH (10 mL) and ethyl acetate (10 mL). The resulting mixture was separated and the organic layer was dried with magnesium sulfate, filtered and evaporated under reduced pressure to yield the title compound as a solid.

Workup

  1. customThe resulting mixture was separated
  2. dry with materialthe organic layer was dried with magnesium sulfate
  3. filtrationfiltered
  4. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-756743c2e16a4c14abaed361ee564104
Source dataset
uspto-grants-2013_09
Patent number
US08530475B2

Reaction notes

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