Methanol → HCID 21471820, compound

HRID 1734082Notes

Reaction equation

HRID 1734082 reaction equation
[F:1][C:2]1[CH:31]=[CH:30][C:5]2[C:6]([CH:9]3[CH2:14][CH2:13][N:12]([CH2:15][C:16]([C:18]4[C:22]5[C:23](=[O:28])[NH:24][CH2:25][CH2:26][CH2:27][C:21]=5[S:20][C:19]=4[CH3:29])=[O:17])[CH2:11][CH2:10]3)=[N:7][O:8][C:4]=2[CH:3]=1.[C:32]([O-])(=O)[C:33]([O-:35])=[O:34].[BH4-].[Na+].C[OH:41]>>[OH2:8].[C:23]([OH:28])(=[O:41])/[CH:22]=[CH:32]/[C:33]([OH:35])=[O:34].[C:23]([OH:28])(=[O:41])/[CH:22]=[CH:32]/[C:33]([OH:35])=[O:34].[F:1][C:2]1[CH:31]=[CH:30][C:5]2[C:6]([CH:9]3[CH2:10][CH2:11][N:12]([CH2:15][CH:16]([C:18]4[C:22]5[C:23](=[O:28])[NH:24][CH2:25][CH2:26][CH2:27][C:21]=5[S:20][C:19]=4[CH3:29])[OH:17])[CH2:13][CH2:14]3)=[N:7][O:8][C:4]=2[CH:3]=1

Participants

5

Reactant 4

HCID 887MethanolHCID 71081OxalateHCID 4311764Sodium borohydrideHCID 21471929HCID 21471929, compound

Product 1

HCID 21471820HCID 21471820, compound

Procedure

To a solution of 0.4 g of 3-(2-(4-(6-fluoro-1,2-benzisoxazol-3-yl)piperidin-1-yl)acetyl)-2-methyl-5,6,7,8-tetrahydro-4H-thieno[3,2-c]azepin-4-one (m.p. 175°-176° C. as oxalate thereof) in 20 ml of methanol was added 0.5 g of sodium borohydride under cooling. The mixture was stirred for 10 minutes and concentrated. Water was added thereto and the solution was extracted with ethyl acetate. The extract was washed with water, dried and the solvent was distilled away. The residue was treated with fumaric acid in ethanol and recrystallized from ethanol to give 0.22 g of 3-(2-(4-(6-fluoro-1,2-benzisoxazol-3-yl)piperidin-1-yl)-1-hydroxyethyl)-2-methyl-5,6,7,8-tetrahydro-4H-thieno[3,2-c]azepin-4-one difumarate monohydrate, m.p. 116°-118° C.

Workup

  1. temperatureunder cooling
  2. concentrationconcentrated
  3. additionWater was added
  4. extractionthe solution was extracted with ethyl acetate
  5. washThe extract was washed with water
  6. customdried
  7. distillationthe solvent was distilled away
  8. additionThe residue was treated with fumaric acid in ethanol
  9. customrecrystallized from ethanol

Sources & evidence

ORD record
ord-e643df3ba6804efcbcf6be23733c6c80
Source dataset
uspto-grants-1996_07
Patent number
US05532240

Reaction notes

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