Water → HCID 13808698, compound

HRID 648708Notes

Reaction equation

HRID 648708 reaction equation
[O:1]=[C:2]1[CH2:8][CH2:7][C:6]2[CH:9]=[CH:10][CH:11]=[CH:12][C:5]=2[S:4][C:3]1([CH2:17][CH2:18][CH2:19][N:20]1[CH2:25][CH2:24][N:23]([C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)[CH2:22][CH2:21]1)[C:13]([O:15][CH3:16])=[O:14].[BH4-].[Na+].O>CO>[OH:1][CH:2]1[CH2:8][CH2:7][C:6]2[CH:9]=[CH:10][CH:11]=[CH:12][C:5]=2[S:4][C:3]1([CH2:17][CH2:18][CH2:19][N:20]1[CH2:25][CH2:24][N:23]([C:26]2[CH:27]=[CH:28][CH:29]=[CH:30][CH:31]=2)[CH2:22][CH2:21]1)[C:13]([O:15][CH3:16])=[O:14]

Participants

5

Reactant 3

HCID 962WaterHCID 4311764Sodium borohydrideHCID 14127335HCID 14127335, compound

Product 1

HCID 13808698HCID 13808698, compoundYield 74.7%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 0.2 g of methyl 3-oxo-2-[3-(4-phenyl-1-piperazinyl)propyl]-2,3,4,5-tetrahydro-1-benzothiepin-2-carboxylate obtained in Example 2 in 20 ml of methanol, 50 mg of sodium borohydride is added in small portions with stirring. After stirring for one hour, the reaction mixture is treated with water and extracted with ethyl acetate. The organic layer is washed with water, dried, and evaporated under reduced pressure. The residue is recrystallized from ethyl acetate-hexane, to give 0.15 g of methyl 3-hydroxy-2-[3-(4-phenyl-1-piperazinyl)propyl]-2,3,4,5-tetrahydro-1-benzothiepin-2-carboxylate as crystals, obtained in Example 7: m.p. 152°-154° C.

Workup

  1. stirringAfter stirring for one hour
  2. extractionextracted with ethyl acetate
  3. washThe organic layer is washed with water
  4. customdried
  5. customevaporated under reduced pressure
  6. customThe residue is recrystallized from ethyl acetate-hexane

Sources & evidence

ORD record
ord-fa4a777d9af242d1bcb6f3d918f8ca2a
Source dataset
uspto-grants-1988_04
Patent number
US04736031

Reaction notes

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