Water → 8-Chloro-5,11-dihydro[1]benzothiepino[4,3-b]pyridin-11-ol

HRID 1647250Notes

Reaction equation

HRID 1647250 reaction equation
[BH4-].[Na+].[Cl:3][C:4]1[CH:19]=[CH:18][C:7]2[C:8](=[O:17])[C:9]3[C:14]([CH2:15][S:16][C:6]=2[CH:5]=1)=[CH:13][CH:12]=[CH:11][N:10]=3.O>CO>[Cl:3][C:4]1[CH:19]=[CH:18][C:7]2[CH:8]([OH:17])[C:9]3[C:14]([CH2:15][S:16][C:6]=2[CH:5]=1)=[CH:13][CH:12]=[CH:11][N:10]=3

Participants

5

Reactant 3

HCID 962WaterHCID 4311764Sodium borohydrideHCID 152802298-Chloro-5,11-dihydro[1]benzothiepino[4,3-b]pyridin-11-one

Product 1

HCID 152802348-Chloro-5,11-dihydro[1]benzothiepino[4,3-b]pyridin-11-olYield 64.2%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Add sodium borohydride (2.60 g, 0.0688 mol) portionwise over 15 minutes to a stirred suspension of 8-chloro-5,11-dihydro[1]benzothiepino[4,3-b]pyridin-11-one (15.0 g, 0.0573 mol) in methanol (150 mL) at 25°-35° C. and under an atmosphere of nitrogen. Stir the mixture for 40 minutes at 25°-30° C. Concentrate the mixture in vacuo to provide a suspension, and then pour it into water (150 mL), and extract with CH2Cl2 (3×100 mL). Combine the extracts, wash with water (3×75 mL), dry over Na2SO4, filter, and concentrate in vacuo. Purify the crude product (18.4 g) via flash chromatography by eluting with EtOAc/hexanes (1:1) to obtain the title compound (9.70 g, 64% yield).

Workup

  1. concentrationConcentrate the mixture in vacuo
  2. customto provide a suspension
  3. extractionextract with CH2Cl2 (3×100 mL)
  4. washCombine the extracts, wash with water (3×75 mL)
  5. dry with materialdry over Na2SO4
  6. filtrationfilter
  7. concentrationconcentrate in vacuo
  8. customPurify the crude product (18.4 g) via flash chromatography
  9. washby eluting with EtOAc/hexanes (1:1)

Sources & evidence

ORD record
ord-1b4e563a334940ea97e79ee3388ac21c
Source dataset
uspto-grants-1995_07
Patent number
US05430032

Reaction notes

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